Haloether and method for producing the same, and vinyl ether and method for producing the same

Abstract

To provide: a vinyl ether and a simple method for producing the same; and a haloether and a method for producing the same, the haloether being used in the method for producing the vinyl ether.SOLUTION: The problem can be solved by producing a haloether by a method comprising a step 1a in which a compound represented by the formula (1) [where Y+ is a cation; and R1 is an organic group] is caused to act on a compound represented by the formula (2a) [where R2a and R3a are each independently H or an alkyl group; R4a is H, halogen, or an organic group; and X1a is halogen other than F] in the presence of a halogenating agent.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to haloethers and methods for producing the same, vinyl ethers and methods for producing the same, and the like.

Background Art

[0002] Conventional synthetic methods of fluorovinyl ethers require multiple steps. Specifically, after reacting an acid fluoride with a fluoride salt to synthesize a salt of fluoroalkoxide, 1) a substitution reaction with ethyl bromofluoroacetate, 2) a reduction reaction using LiAlH4, 3) a tosylation reaction using tosyl chloride and pyridine, and 4) a reaction for eliminating p-toluenesulfonic acid with lithium(bistrimethylsilyl)amide (LiHMDS) are carried out to synthesize fluorovinyl ether (Non-Patent Document 1).

Prior Art Documents

Non-Patent Documents

[0003]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] The synthetic method of fluorovinyl ether in Non-Patent Document 1 involves multiple steps, and there is room for improvement in terms of simplifying the synthetic method.

[0005] The present disclosure provides vinyl ethers and simple methods for producing the same, and haloethers used in the method for producing vinyl ethers and methods for producing the same, and the like.

Means for Solving the Problems

[0006] The present disclosure includes the following aspects. Item 1. Formula (4a): [Chemical formula] [wherein, R 1 is an organic group, R 2a and R 3a are each independently H or an alkyl group, R 4a is H, a halogen, or an organic group, X 1a is a halogen other than F, X 2 is a halogen. ] A method for producing a compound represented by Formula (1): [Chemical formula] [wherein, Y + is a cation, R 1 has the same meaning as defined above. ] The compound represented by [Chemical formula] [wherein the symbols have the same meaning as defined above. ] is reacted with a compound represented by Formula (2a): Item 2. The halogenating agent is represented by Formula (3a): X 2 -Z (3a) [wherein, X 2 is a halogen, Z is a halogen or NZ 1 Z 2 and Z 1 and Z 2 are each independently an organic group, or Z 1 and Z 2 are bonded to each other to form a ring. ] Or Formula (3a'): [Chemical formula] [In the formula, X 2 is a halogen, Q 1 ~Q 4 are each independently H or an organic group, and any two of Q 1 ~Q 4 may be bonded to each other to form a ring.] The production method according to claim 1, which is a compound represented by . Claim 3. Y + is a metal ion or a quaternary ammonium ion, the production method according to claim 1 or 2. Claim 4. R 1 is an optionally substituted fluoroalkyl group, and the fluoroalkyl group may contain a heteroatom between carbon atoms. The production method according to any one of claims 1 to 3. Claim 5. R 1 is an optionally substituted C 1-10 fluoroalkyl group, and the C 1-10 fluoroalkyl group may contain a heteroatom between carbon atoms. The production method according to any one of claims 1 to 4. Claim 6. R 4a is F or a fluoroalkyl group. The production method according to any one of claims 1 to 5. Claim 7. R 2a and R 3a are each independently H or a C 1-3 alkyl group. The production method according to any one of claims 1 to 6. Claim 8. The production method according to any one of claims 1 to 7, wherein the step 1a is carried out in the absence of a catalyst. Claim 9. Formula (4b): [Chemical formula] [In the formula, R 1is an organic group, R 2b and R 3b are each independently H, a halogen, or an alkyl group which may have one or more substituents, R 4b is H, a halogen, or an organic group, X 1b and X 2 are each independently a halogen.] A process for producing a compound represented by Formula (1):

Chemical formula

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Chemical formula

Chemical formula

Chemical formula

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Chemical formula

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Chemical formula

[0007] According to the present disclosure, there are provided vinyl ether, a simple production method thereof, a haloether used in the production method of vinyl ether, and a production method thereof, etc. [Modes for Carrying Out the Invention]

[0008] The above summary of the present disclosure is not intended to describe each disclosed embodiment or all implementations of the present disclosure. The following description of the present disclosure more specifically illustrates exemplary embodiments. In some places of the present disclosure, guidance is provided through examples, and these examples can be used in various combinations. In each case, the group of examples can function as a non-exclusive and representative group. All publications, patents, and patent applications cited in this specification are hereby incorporated by reference in their entirety.

[0009] 1. Terms Unless otherwise specified, the symbols and abbreviations in this specification can be understood in the meaning commonly used in the technical field to which the present disclosure belongs, in accordance with the context of this specification. In this specification, the term "comprising" is used with the intention of including the terms "consisting essentially of" and "consisting of". Unless otherwise particularly limited, the steps, processes, or operations described in this specification can be carried out at room temperature. In this specification, room temperature can mean a temperature within the range of 10 to 40°C. In this specification, the notation "C n-m"(where n and m are each a number) represents, as is commonly understood by those skilled in the art, having a carbon number of n or more and m or less." In this specification, the phrase "compound represented by formula (N)" may be referred to as compound (N).

[0010] In this specification, "organic group" means a group containing one or more carbon atoms. Examples of the said "organic group" are a hydrocarbon group which may have one or more substituents, an alkyl group which may have one or more substituents, an alkenyl group which may have one or more substituents, an alkynyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, a cycloalkenyl group which may have one or more substituents, a cycloalkadienyl group which may have one or more substituents, an aryl group which may have one or more substituents, an aralkyl group which may have one or more substituents, a non-aromatic heterocyclic group which may have one or more substituents, a heteroaryl group which may have one or more substituents, a cyano group, an aldehyde group, R r O-, R r S-, R r NH-, (R r )2N-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R r OSO2- (In these formulas, R r is independently an alkyl group which may have one or more substituents, an alkenyl group which may have one or more substituents, an alkynyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, a cycloalkenyl group which may have one or more substituents, a cycloalkadienyl group which may have one or more substituents, an aryl group which may have one or more substituents, an aralkyl group which may have one or more substituents, a non-aromatic heterocyclic group which may have one or more substituents, or a heteroaryl group which may have one or more substituents.) can be included.

[0011] In the present specification, unless otherwise particularly limited, examples of the "hydrocarbon group" can include an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkadienyl group, an aryl group, an aralkyl group, and a group which is a combination of these.

[0012] In the present specification, unless otherwise particularly limited, examples of the "alkyl group" include linear or branched C alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl, nonyl, and decyl. 1-12 can be included.

[0013] In the present specification, unless otherwise particularly limited, examples of the "alkenyl group" include linear or branched C alkenyl groups such as vinyl, 1-propen-1-yl, 2-propen-1-yl, isopropenyl, 2-buten-1-yl, 4-penten-1-yl, and 5-hexen-1-yl. 2-10 can be included.

[0014] In this specification, unless otherwise particularly limited, examples of the "alkynyl group" include linear or branched C such as ethynyl, 1-propyn-1-yl, 2-propyn-1-yl, 4-pentyn-1-yl, 5-hexyn-1-yl, etc. 2-10 can include an alkynyl group.

[0015] In this specification, unless otherwise particularly limited, examples of the "cycloalkyl group" include C such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. 3-7 can include a cycloalkyl group.

[0016] In this specification, unless otherwise particularly limited, examples of the "cycloalkenyl group" include C such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. 3-7 can include a cycloalkenyl group.

[0017] In this specification, unless otherwise particularly limited, examples of the "cycloalkadienyl group" include C such as cyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cyclononadienyl, cyclodecadienyl, etc. 4-10 can include a cycloalkadienyl group.

[0018] In this specification, unless otherwise particularly limited, the "aryl group" can be monocyclic, bicyclic, tricyclic, or tetracyclic. In this specification, unless otherwise particularly limited, the "aryl group" can be a C 6-18 aryl group. In this specification, unless otherwise particularly limited, examples of the "aryl group" can include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, and 2-anthryl.

[0019] In this specification, unless otherwise particularly limited, examples of the "aralkyl group" can include benzyl, phenethyl, diphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, 2,2-diphenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 2-biphenylylmethyl, 3-biphenylylmethyl, and 4-biphenylylmethyl.

[0020] In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be monocyclic, bicyclic, tricyclic, or tetracyclic. In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be, for example, a non-aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms in addition to carbon atoms as ring-constituting atoms. In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be saturated or unsaturated. In this specification, unless otherwise particularly limited, examples of the "non-aromatic heterocyclic group" include tetrahydrofuryl, oxazolidinyl, imidazolinyl (e.g., 1-imidazolinyl, 2-imidazolinyl, 4-imidazolinyl), aziridinyl (e.g., 1-aziridinyl, 2-aziridinyl), azetidinyl (e.g., 1-azetidinyl, 2-azetidinyl), pyrrolidinyl (e.g., 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl), piperidinyl (e.g., 1-piperidinyl, 2-piperidinyl, 3-piperidinyl), azepanyl (e.g., 1-azepanyl, 2-azepanyl, 3-azepanyl, 4-azepanyl), azocanyl (e.g., 1-azocanyl, 2-azocanyl, 3-azocanyl, 4-azocanyl), piperazinyl (e.g., 1,4-piperazin-1-yl, 1,4-piperazin-2-yl), diazepinyl (e.g., 1,4-diazepin-1-yl, 1,4-diazepin-2-yl, 1,4-diazepin-5-yl, 1,4-diazepin-6-yl), diazocanyl (e.g., 1,4-diazocan-1-yl, 1,4-diazocan-2-yl, 1,4-diazocan-5-yl, 1,4-diazocan-6-yl, 1,5-diazocan-1-yl, 1,5-diazocan-2-yl, 1,5-diazocan-3-yl), tetrahydropyranyl (e.g., tetrahydropyran-4-yl), morpholinyl (e.g., 4-morpholinyl), thiomorpholinyl (e.g., 4-thiomorpholinyl), 2-oxazolidinyl, dihydrofuryl, dihydropyranyl, and dihydroquinolyl, etc.

[0021] In this specification, unless otherwise particularly limited, examples of the "heteroaryl group" can include monocyclic aromatic heterocyclic groups (e.g., 5- or 6-membered monocyclic aromatic heterocyclic groups), and aromatic condensed heterocyclic groups (e.g., 5- to 18-membered aromatic condensed heterocyclic groups).

[0022] In this specification, unless otherwise particularly limited, examples of the "5- or 6-membered monocyclic aromatic heterocyclic group" include pyrrolyl (e.g., 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl), furyl (e.g., 2-furyl, 3-furyl), thienyl (e.g., 2-thienyl, 3-thienyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl), imidazolyl (e.g., 1-imidazolyl, 2-imidazolyl, 4-imidazolyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl), thiazolyl (e.g., 2-thiazolyl, 4-thiazolyl, 5-thiazolyl), triazolyl (e.g., 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl), oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl), thiadiazolyl (e.g., 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl), tetrazolyl, pyridyl (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl), pyridazinyl (e.g., 3-pyridazinyl, 4-pyridazinyl), pyrimidinyl (e.g., 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl), pyrazinyl, etc.

[0023] In this specification, unless otherwise particularly limited, examples of the "5- to 18-membered aromatic condensed heterocyclic group" include isoindolyl (e.g., 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl), indolyl (e.g., 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl), benzofuranyl (e.g., 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl), benzocfuranyl (e.g., 1-benzocfuranyl, 4-benzocfuranyl, 5-benzocfuranyl), benzothienyl, (e.g., 2-benzothienyl, 3-benzothienyl, 4-benzothienyl, 5-benzothienyl, 6-benzothienyl, 7-benzothienyl), benzocthienyl (e.g., 1-benzocthienyl, 4-benzocthienyl, 5-benzocthienyl), indazolyl (e.g., 1-indazolyl, 2-indazolyl, 3-indazolyl, 4-indazolyl, 5-indazolyl, 6-indazolyl, 7-indazolyl), benzimidazolyl (e.g., 1-benzimidazolyl, 2-benzimidazolyl, 4-benzimidazolyl, 5-benzimidazolyl), 1,2-benzisoxazolyl (e.g., 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl), benzoxazolyl (e.g., 2-benzoxazolyl, 4-benzoxazolyl, 5-benzoxazolyl, 6-benzoxazolyl, 7-benzoxazolyl), 1,2-benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,(2-benzisothiazol-7-yl), benzothiazolyl (e.g., 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7-benzothiazolyl), isoquinolyl (e.g., 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl), quinolyl (e.g., 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 8-quinolyl), cinnolinyl (e.g., 3-cinnolinyl, 4-cinnolinyl, 5-cinnolinyl, 6-cinnolinyl, 7-cinnolinyl, 8-cinnolinyl), phthalazinyl (e.g., 1-phthalazinyl, 4-phthalazinyl, 5-phthalazinyl, 6-phthalazinyl, 7-phthalazinyl, 8-phthalazinyl), quinazolinyl (e.g., 2-quinazolinyl, 4-quinazolinyl, 5-quinazolinyl, 6-quinazolinyl, 7-quinazolinyl, 8-quinazolinyl), quinoxalinyl (e.g., 2-quinoxalinyl, 3-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 7-quinoxalinyl, 8-quinoxalinyl), pyrazolo[1,5-a]pyridyl (e.g., pyrazolo[1,5-a]pyridin-2-yl, pyrazolo[1,5-a]pyridin-3-yl, pyrazolo[1,5-a]pyridin-4-yl, pyrazolo[1,5-a]pyridin-5-yl, pyrazolo[1,5-a]pyridin-6-yl, pyrazolo[1,5-a]pyridin-7-yl), imidazo[1,2-a]pyridyl (e.g., imidazo[1,2-a]pyridin-2-yl, imidazo[1,2-a]pyridin-3-yl, imidazo[1,2-a]pyridin-5-yl, imidazo[1,2-a]pyridin-6-yl, imidazo[1,2-a]pyridin-7-yl, imidazo[1,2-a]pyridin-8-yl), etc. can be included.,

[0024] In this specification, "R r Examples of "O-" are alkoxy (e.g., C such as methoxy, ethoxy, propoxy, etc. 1-10 alkoxy), cycloalkoxy (e.g., C such as cyclopentoxy, cyclohexoxy, etc. 3-7 cycloalkoxy), aryloxy (e.g., C such as phenoxy, naphthoxy, etc. 6-18 aryloxy), and aralkyloxy (e.g., C such as benzyloxy, phenethyloxy, etc. 7-19It may include (aralkyloxy).

[0025] In this specification, examples of "R r S-" may include alkoxylthio (e.g., C such as methylthio, ethylthio, propylthio, etc.) 1-10 alkylthio), cycloalkylthio (e.g., C such as cyclopentylthio, cyclohexylthio, etc.) 3-7 cycloalkylthio), arylthio (e.g., C such as phenylthio, naphthylthio, etc.) 6-18 arylthio), and aralkylthio (e.g., C such as benzylthio, phenethylthio, etc.) 7-19 aralkylthio).

[0026] In this specification, examples of "R r NH-" may include monoalkylamino (e.g., mono-C such as monomethylamino, monoethylamino, monopropylamino, etc.) 1-10 alkylamino), monocycloalkylamino (e.g., mono-C such as monocyclopentylamino, monocyclohexylamino, etc.) 3-7 cycloalkylamino), monoarylamino (e.g., mono-C such as monophenylamino, mononaphthylamino, etc.) 6-18 arylamino), and monoaralkylamino (e.g., mono-C such as monobenzylamino, monophenethylamino, etc.) 7-19 aralkylamino).

[0027] In this specification, examples of "(R r )2N-" may include dialkylamino (e.g., di-C such as dimethylamino, ethylmethylamino, diethylamino, etc.) 1-10 alkylamino), N-aryl-N-alkylamino (e.g., N-C such as N-phenyl-N-methylamino, etc.) 6-18 aryl-N-C 1-10 alkylamino), and diarylamino (e.g., di-C such as diphenylamino, etc.) 6-18 arylamino).

[0028] In this specification, examples of "R r CO-" may include alkylcarbonyl [e.g., (C such as acetyl, propionyl, butyryl, etc.)1-10 (alkyl)carbonyl], cycloalkylcarbonyl [e.g., (C such as cyclopentanoyl, cyclohexanoyl, etc.) 3-7 cycloalkyl)carbonyl], arylcarbonyl [e.g., (C such as benzoyl, naphthoyl, etc.) 6-18 aryl)carbonyl], and aralkylcarbonyl [e.g., (C such as benzylcarbonyl, phenethylcarbonyl, etc.) 7-19 aralkyl)carbonyl] can be included.

[0029] In this specification, "R r Examples of "COO-" are alkylcarbonyloxy [e.g., (C such as acetyloxy, propionyloxy, butyryloxy, etc.) 1-10 alkyl)carbonyloxy], cycloalkylcarbonyloxy [e.g., (C such as cyclopentanoyloxy, cyclohexanoyloxy, etc.) 3-7 cycloalkyl)carbonyloxy], arylcarbonyloxy [e.g., (C such as benzoyloxy, naphthoyloxy, etc.) 6-18 aryl)carbonyloxy], and aralkylcarbonyloxy [e.g., (C such as benzylcarbonyloxy, phenethylcarbonyloxy, etc.) 7-19 aralkyl)carbonyloxy] can be included.

[0030] In this specification, "R r Examples of "SO2-" are alkylsulfonyl (e.g., C such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, etc.) 1-10 alkylsulfonyl), cycloalkylsulfonyl (e.g., C such as cyclopentylsulfonyl, cyclohexylsulfonyl, etc.) 4-8 cycloalkylsulfonyl), arylsulfonyl (e.g., C such as phenylsulfonyl, naphthylsulfonyl, etc.) 6-18 arylsulfonyl), and aralkylsulfonyl (e.g., C such as benzylsulfonyl, phenethylsulfonyl, etc.) 7-19 aralkylsulfonyl] can be included.

[0031] In this specification, "R rExamples of "OCO-" include alkoxycarbonyl [(C 1-10 such as (C 3-7 alkoxy)carbonyl] like methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc., cycloalkoxycarbonyl [(C 6-18 such as (C 7-19 cycloalkoxy)carbonyl] like cyclopentoxycarbonyl, cyclohexoxycarbonyl, etc., aryloxycarbonyl [(C

[0032] such as (C r aryloxy)carbonyl] like phenoxycarbonyl, naphthoxycarbonyl, etc., and aralkyloxycarbonyl [(C 1-10 such as (C 3-7 cycloalkoxysulfonyl) like cyclopentoxysulfonyl, cyclohexoxysulfonyl, etc., aryloxysulfonyl [(C 6-18 such as (C 7-19 aralkyloxy)carbonyl] like benzyloxycarbonyl, phenethyloxycarbonyl, etc. can be included.

[0033] In this specification, "a hydrocarbon group which may have one or more substituents", "an alkyl group which may have one or more substituents", "an alkenyl group which may have one or more substituents", "an alkynyl group which may have one or more substituents", "a cycloalkyl group which may have one or more substituents", "a cycloalkenyl group which may have one or more substituents", "a cycloalkadienyl group which may have one or more substituents", "an aryl group which may have one or more substituents", "an aralkyl group which may have one or more substituents", "a non-aromatic heterocyclic group which may have one or more substituents", and "a heteroaryl group which may have one or more substituents" Examples of the "substituent" in each of them are, respectively, a halo group, a nitro group, a cyano group, an oxo group, a thioxo group, a sulfo group, a sulfamoyl group, a sulfinamoyl group, a sulfenamoyl group, R r O-, R r S-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R r OSO2- (in these formulas, R r is as defined above.) can be included.

[0034] Among the substituents, examples of the "halo group" can include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0035] The number of the substituents can be within the range from 1 to the maximum number that can be substituted (e.g., 1, 2, 3, 4, 5, 6).

[0036] 2. Method for Producing the Compound Represented by Formula (4a) In one embodiment, the method for producing the compound represented by formula (4a) includes step 1a of allowing the compound represented by formula (1) to act on the compound represented by formula (2a) in the presence of a halogenating agent.

[0037] 2-1. Compound Represented by Formula (1) In formula (1), R 1 is not particularly limited as long as it can form an oxide. R 1is a hydrocarbon group which may preferably have one or more substituents (the hydrocarbon group may contain a hetero atom between carbon atoms), and more preferably an alkyl group which may preferably have one or more substituents (the alkyl group may contain a hetero atom between carbon atoms). The "one or more substituents" that the hydrocarbon group and the alkyl group may have preferably include a halo group, and more preferably include a fluoro group. That is, R 1 is a haloalkyl group which may preferably have one or more substituents (the haloalkyl group may contain a hetero atom between carbon atoms), and more preferably a fluoroalkyl group which may preferably have one or more substituents (the fluoroalkyl group may contain a hetero atom between carbon atoms). The fluoroalkyl group may be a perfluoroalkyl group. The "one or more substituents" that the haloalkyl group and the fluoroalkyl group may have preferably include a nitrile group, an ester group (e.g., R r OCO-), a formyl group, and a sulfonyl-containing group (e.g., R r OSO2-). Examples of the "hetero atom" that may be included between carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group include, but are not limited to, an oxygen atom, a sulfur atom, a nitrogen atom, etc. The number of carbon atoms of the hydrocarbon, alkyl group, haloalkyl group, and fluoroalkyl group is not particularly limited as long as it is 1 or more, and is, for example, in the range of 1 to 12, preferably in the range of 1 to 9, more preferably in the range of 1 to 6, and most preferably in the range of 1 to 4.

[0038] Examples of the "fluoroalkyl group which may preferably have one or more substituents (the fluoroalkyl group may contain a hetero atom between carbon atoms)" include, for example, CF3- CH3-CF2- CHF2-CH2- CF3-CH2- CF3-CF2- CF3-CF2-CH2- CF3-CF2-CF2- (CF3)2CF-、 CF3-O-CF2-、 CF3-O-CF(CF3)-、 CF3-CF2-CF2-CF2-、 CF3-CF2-CF(CF3)-CF2-、 CF3-O-CH2-CH2-、 CF3-O-CH(CF3)-CH2-、 CF3-O-CF2-CF2-、 (CF3CF2)(CF2)CF-、 (CF3)3C-、 CF3-CF2-O-CF2-、 CF3-CF2-CF2-CF2-CF2-、 CF3-CF2-O-CF2-CF2-、 CF3-O-CF2-O-CF2-、 CF3-CF2-CF2-CF2-CF2-CF2-、 CF3-CF2-CF2-O-CH2-CF2-、 CF3-CF2-CF2-O-CF2-CF2-、 CF3-CF2-CF2-CF2-CF2-CF2-CF2-、 CF3-CF2-CF2-CF2-CF2-CF2-CF2-CF2-、 CHF2-CF2-CF2-CF2-CF2-CF2-CF2-CH2- CF3-CF(CF3)-CF2-、 CF3-CF2-CF(CF3)-、 CF3-CF2-CF2-O-CF(CF3)-CF2-、 CF3-CF2-CF2-O-CF(CF3)-CF2-O-CF(CF3)-CF2-、 CF3-CF2-CF2-O-[CF(CF3)-CF2-O-]2-CF(CF3)-CF2- etc. fluoro C 1-10 alkyl group, fluoro C 1-3 alkoxy fluoro C 1-3 alkyl group, fluoro C 1-3 alkoxy fluoro C 1-3 alkoxy fluoro C1-3 An alkyl group, a fluoro C 1-3 An alkoxyfluoro C 1-3 An alkoxyfluoro C 1-3 An alkoxyfluoro C 1-3 Examples include an alkyl group and the like.

[0039] In formula (1), Y + is not particularly limited as long as it can be a counter ion of R 1 O - . Y + is, for example, a metal ion or formula (1a):

Chemical formula

[0040] The metal ion includes a monovalent or divalent metal ion, and specific examples thereof include, for example, lithium, sodium, potassium, cesium, silver, and the like.

[0041] In formula (1a), Y 1 ~Y 4 is not particularly limited as long as it can form a nitrogen-containing ion. Y 1 ~Y 4Each of them is preferably a hydrocarbon group which may have H or one or more substituents, more preferably H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, still more preferably an alkyl group which may have one or more substituents, and particularly preferably a C 1-4 alkyl group. Examples of the "substituents" that the hydrocarbon group, alkyl group, cycloalkyl group, aryl group, and aralkyl group may have include, but are not limited to, a halo group, a hydroxyl group, a mercapto group, etc.

[0042] Y 1 ~Y 4 Examples of the ring formed by any two of them bonding to each other include, but are not limited to, 5- or 6-membered rings such as pyrrolidine, piperidine, and morpholine.

[0043] Y + is a metal ion, or, in formula (1a), Y 1 ~Y 4 is preferably a quaternary ammonium ion such as an ion in which all are other than H. The metal ion is, for example, a monovalent or divalent metal ion, preferably a monovalent or divalent metal ion selected from the group consisting of alkali metals, alkaline earth metals, and transition metal groups, and still more preferably lithium, sodium, potassium, cesium, or silver is preferably used.

[0044] The compound represented by formula (1) may be used directly as itself, but formula (1') or formula (1''): R 1 -COF (1') R 1 -O―CH3(1'') [wherein, R 1 is as defined above. However, in formula (1''), R 1 is R 1 '-CF2, and R 1’ is an organic group. The compound represented by the formula (1) may be generated in the reaction system from a compound represented by the following formula or the like. Specifically, the compound represented by the formula (1) can be produced by reacting the compound represented by the formula (1’) with a fluorinating agent. That is, as the reactants in steps 1a and 1b, instead of directly using the compound represented by the formula (1), the compound represented by the formula (1’) and a fluorinating agent can be used. Examples of the fluorinating agent include F - Y + (Y + has the same meaning as described above.) and is preferably an alkali metal fluoride such as potassium fluoride, rubidium fluoride, cesium fluoride, or a tetra-C 1-4 alkylammonium fluoride such as tetramethylammonium fluoride or tetraethylammonium fluoride. In addition, the compound represented by the formula (1) can be produced by reacting the compound represented by the formula (1’’) with an amine. That is, as the reactants in steps 1a and 1b, instead of directly using the compound represented by the formula (1), the compound represented by the formula (1’) and an amine can be used. Examples of the amine include trimethylamine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dimethylbenzylamine, N-methylmorpholine, tetramethylethylenediamine, N,N’-dimethylpiperazine, and the like. For this method, reference can be made to, for example, International Publication No. 2014 / 110329.

[0045] R 1 ’ is, similar to R 1 , preferably a hydrocarbon group which may have one or more substituents (the hydrocarbon group may contain a heteroatom between carbon atoms), and more preferably an alkyl group which may have one or more substituents (the alkyl group may contain a heteroatom between carbon atoms). The “one or more substituents” that the hydrocarbon group and the alkyl group may have preferably include a halo group, and more preferably include a fluoro group. That is, R 1' is preferably a haloalkyl group which may have one or more substituents (the haloalkyl group may contain a heteroatom between carbon atoms), more preferably a fluoroalkyl group which may have one or more substituents (the fluoroalkyl group may contain a heteroatom between carbon atoms). The fluoroalkyl group may be a perfluoroalkyl group. The "one or more substituents" that the haloalkyl group and the fluoroalkyl group may have preferably include a nitrile group, an ester group (e.g., R r OCO-), a formyl group, and a sulfonyl-containing group (e.g., R r OSO2-). Examples of the "heteroatom" that may be included between carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group include, but are not limited to, an oxygen atom, a sulfur atom, a nitrogen atom, etc. The number of carbon atoms of the hydrocarbon, alkyl group, haloalkyl group, and fluoroalkyl group is not particularly limited as long as it is 1 or more, and is, for example, in the range of 1 to 11, preferably in the range of 1 to 8, more preferably in the range of 1 to 5, and most preferably in the range of 1 to 3.

[0046] The compound represented by formula (1) can be used alone or in combination of two or more.

[0047] 2-2. Compound Represented by Formula (2a) In formula (2a), each of R 2a and R 3a is preferably H or a C 1-6 alkyl group, more preferably H or a C 1-4 alkyl group, and even more preferably H or a C 1-3 alkyl group. In one embodiment, (I) both R 2a and R 3a are H, (II) R 2a is H and R 3a is a C 1-3 alkyl group, or (III) both R 2a and R 3a are C 1-3 alkyl groups are preferred.

[0048] In formula (2a), R 4a is preferably a halogen or a hydrocarbon group which may have one or more substituents, more preferably a halogen or an alkyl group which may have one or more substituents. The "substituent" which the hydrocarbon group and the alkyl group may have preferably includes a halo group, and more preferably includes a fluoro group.

[0049] R 4a is preferably a halogen or a haloalkyl group, more preferably F or a fluoroalkyl group, still more preferably F or a fluoroC 1-6 alkyl group, and even more preferably F or a fluoroC 1-4 alkyl group, particularly preferably F or a fluoroC 1-3 alkyl group.

[0050] X 1a is a halogen other than F, but the reaction of step 1a can proceed. X 1a is preferably Cl, Br, or I, and more preferably Cl or Br.

[0051] The compound represented by formula (2a) can be used alone or in combination of two or more.

[0052] The amount of the compound represented by formula (2a) used is not particularly limited. The lower limit of the amount used is, for example, 0.5 mol or more, preferably 1 mol or more, more preferably 3 mol or more, still more preferably 5 mol or more, per 1 mol of the compound represented by formula (1). The upper limit of the amount used is, for example, 50 mol or less, preferably 40 mol or less, more preferably 30 mol or less, per 1 mol of the compound represented by formula (1). The amount used can be in the range of any combination of the lower limit and the upper limit. When the compound represented by formula (2a) is used in excess, the unreacted compound represented by formula (2a) can be recovered and used further.

[0053] 2-3. Halogenating Agent The halogenating agent is not particularly limited as long as it can introduce a halogen into the carbon atom substituted by R and R in the compound represented by the formula (2a). Examples of the halogenating agent include compounds represented by the formula (3a) or (3a’). 2a and R 3a in the compound represented by the formula (2a).

[0054] In the formula (3a), X 2 is preferably Cl, Br, or I.

[0055] In the formula (3a), when Z is a halogen, X 2 may be the same as or different from it. The halogen is preferably Cl, Br, or I. Examples of the halogenating agent in which Z is a halogen in the formula (3a) include I2, Br2, ICl, BrI, etc.

[0056] When Z is NZ 1 Z 2 each of Z 1 and Z 2 is preferably an alkyl group, an alkylcarbonyl group, or an alkylsulfonyl group.

[0057] When Z is NZ 1 Z 2When it is, the halogenating agent is, for example, an N-haloamide compound. The N-haloamide compound is preferably a primary amide, a secondary amide, or a combination thereof. The primary amide or secondary amide is preferably a carboxamide, a sulfonamide, a lactam, a carbamate, an imide, a ureido, or a combination thereof. Examples of the amide include halogenated 5,5-dimethylhydantoin, 3-benzyl-5,5-dimethylhydantoin, 5-methyl-5-phenylhydantoin, 5,5-diphenylhydantoin, 5,5-hexamethylenehydantoin, 5,5-pentamethylenehydantoin, 5,5-tetramethylenehydantoin, succinimide, phthalimide, saccharin, isocyanuric acid, 5,5-dimethylbarbituric acid, glycoluril, 3a,6a-diphenylglycoluril, 3a,6a-dimethylglycoluril, 4,4,5,5-tetramethyl-2-imidazolidinone, 4,4-dimethyl-2-oxazolidinone, and the like.

[0058] The primary amide is, for example, a carboxamide. Examples of the primary carboxamide include the following: Z such as lactam or peptide 8 C(=O)NX 2 Z 9 ; t-BuX 2 Z such as NBoc, 2-oxazolidinone derivative (e.g., 4,4-dimethyl-2-oxazolidinone), etc. 8 NX 2 C(=O)OZ 9 (carbamate); Z such as 2-imidazolidinone derivative (e.g., 4,4,5,5-tetramethyl-2-imidazolidinone), glycoluril and its derivatives (e.g., 3a,6a-diphenylglycoluril, 3a,6a-dimethylglycoluril), etc. 8 NX 2 C(=O)NX 2 Z 9 (derivative of urea) and the like. Note that Z 8 and Z 9is, independently of one another, an alkyl group which may have one or more substituents, and X 2 has the same meaning as described above, and two Xs present in the same molecule 2 may be the same as or different from each other.

[0059] The primary amide is, for example, a sulfonamide, a phosphoramide, or a nitramide. Examples of the sulfonamide include Z 8 S(=O)2NX 2 Z 9 、Z 8 NX 2 S(=O)2NX 2 Z 9 and the like. Examples of the phosphoramide include Z 8 2P(=O)NX 2 Z 9 and the like. Examples of the nitramide include O2N-NX 2 Z 8 and the like. Note that Z 8 、Z 9 、and X 2 have the same meaning as described above.

[0060] The secondary amide is, for example, an imide ([C(=O)]2NX 2 ). Examples of the imide include succinimide, phthalimide and the like. Examples of the secondary amide include Z 8 S(=O)2NX 2 C(=O)Z 9 、Z 8 S(=O)2NX 2 S(=O)2Z 9 、Z 8 X 2 NC(=O)NX 2 C(=O)Z 9 、Z 8 C(=O)NX 2 C(=O)NX 2 C(=O)Z 9 、Z 8 S(=O)2NX 2 C(=O)NX 2 C(=O)Z 9 、Z8 S(=O)2NX 2 C(=O)NX 2 S(=O)2Z 9 (ureide), etc. may be mentioned. Here, Z 8 , Z 9 , and X 2 have the same meanings as described above. Non-limiting examples of ureides include halogenated hydantoin derivatives (e.g., 5,5-dimethylhydantoin, 3-benzyl-5,5-dimethylhydantoin, 5-methyl-5-phenylhydantoin, 5,5-diphenylhydantoin, 5,5-pentamethylenehydantoin, 5,5-hexamethylenehydantoin, 5,5-tetramethylenehydantoin, etc.), isocyanuric acid, barbituric acid derivatives (e.g., 5,5-diethylbarbituric acid, 5,5-dimethylbarbituric acid, 5-ethyl-5-isoamylbarbituric acid, etc.).

[0061] The amide is preferably a sulfonamide, lactam, carbamate, imide, or ureide. Preferred examples of the amide include halogenated 5-dimethylhydantoin, 3-benzyl-5,5-dimethylhydantoin, 5-methyl-5-phenylhydantoin, 5,5-diphenylhydantoin, 5,5-hexamethylenehydantoin, 5,5-pentamethylenehydantoin, 5,5-tetramethylenehydantoin, succinimide, phthalimide, saccharin, isocyanuric acid, 5,5-dimethylbarbituric acid, glycoluril, 3a,6a-diphenylglycoluril, 3a,6a-dimethylglycoluril, 4,4,5,5-tetramethyl-2-imidazolidinone, or 4,4-dimethyl-2-oxazolidinone, etc.

[0062] The halogenating agent is, for example, a mono-halogenated or poly-halogenated amide compound.

[0063] Z is NZ 1 Z 2 and Z 1 and Z 2Examples of the halogenating agent in which they are bonded to each other to form a ring include, for example, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, dichloroisocyanuric acid, dibromoisocyanuric acid, diiodoisocyanuric acid, N-chlorophthalimide, N-bromophthalimide, N-iodophthalimide, N-chlorosaccharin, N-bromosaccharin, N-iodosaccharin, 1-halo-5,5-dimethylhydantoin, 3-halo-5,5-dimethylhydantoin, 2,4,6,8-tetrachloroglycoluril, mixtures thereof, and the like.

[0064] In formula (3a’), Q 1 ~Q 4 is not particularly limited as long as it can form a nitrogen-containing ion. Q 1 ~Q 4 Each of them is preferably H or a hydrocarbon group which may have one or more substituents, more preferably H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, still more preferably an alkyl group which may have one or more substituents, and particularly preferably a C 1-4 alkyl group. Examples of the "substituent" which the hydrocarbon group, alkyl group, cycloalkyl group, aryl group, and aralkyl group may have include, but are not limited to, a halo group, a hydroxyl group, a mercapto group, and the like.

[0065] Q 1 ~Q 4 Examples of the ring formed by bonding any two of Q

[0066] The halogenating agent can be used singly or in combination of two or more.

[0067] The amount of the halogenating agent used is not particularly limited. The lower limit of the amount used is, for example, 0.01 mol or more, preferably 0.05 mol or more, more preferably 0.1 mol or more, per 1 mol of the compound represented by the formula (1). The upper limit of the amount used is, for example, 10 mol or less, preferably 7 mol or less, more preferably 5 mol or less, per 1 mol of the compound represented by the formula (1). The amount used can be in the range of arbitrarily combining the above lower limit and the above upper limit.

[0068] 2-4. Catalyst Step 1a can be carried out in the absence of a catalyst, but it may also be carried out in the presence of a catalyst.

[0069] The catalyst is not particularly limited as long as it catalyzes the reaction. Examples of the catalyst include Lewis bases. Examples of the Lewis base include compounds represented by the formula (3b).

[0070] In the formula (3b), when L 1 is O, (S) m or (Se) k n is 2, and each Z 3 is preferably a hydrocarbon group which may have one or more substituents, more preferably an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and still more preferably an alkyl group which may have one or more substituents, or an aryl group which may have one or more substituents. Examples of the "substituents" which the hydrocarbon group, alkyl group, cycloalkyl group, aryl group, and aralkyl group may have include a halo group, an alkoxy group, and the like.

[0071] When L 1 is N or P, n is 3, and each Z 3is a hydrocarbon group which may preferably have one or more substituents, more preferably an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and still more preferably an alkyl group which may have one or more substituents, or an aryl group which may have one or more substituents.

[0072] Examples of the compound represented by the formula (3b) include, but are not limited to, dialkyl ethers such as diethyl ether; diaryl sulfides such as diphenyl ether; dialkyl sulfides such as dimethyl sulfide; diaryl sulfides such as diphenyl sulfide; dialkyl disulfides such as dimethyl disulfide; diaryl disulfides such as diphenyl disulfide; dialkyl selenides such as dimethyl selenide; diaryl selenides such as diphenyl selenide; dialkyl diselenides such as dimethyl diselenide; diaryl diselenides such as diphenyl diselenide; trialkyl amines such as triethylamine; triaryl amines such as triphenylamine; trialkyl phosphines such as triethylphosphine; triaryl phosphines such as triphenylphosphine, etc.

[0073] In the formula (3c), Z 4 such as, for example, P(Z 5 )3 [each Z 5 is independently an organic group, and any two Z 5 may be bonded to each other to form a ring.], C(Z 6 )2 [each Z 6 is independently an organic group, and two Z 6 may be bonded to each other to form a ring.] etc. may be mentioned.

[0074] Each Z 5is preferably a hydrocarbon group which may have one or more substituents, more preferably an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents.

[0075] Each Z 5 is N(Z 7 )2[Each Z 7 is, independently of one another, an organic group, and the two Z 7 may be bonded to each other to form a ring.] It is also preferable that it is.

[0076] Each Z 7 is preferably a hydrocarbon group which may have one or more substituents, more preferably an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and still more preferably an alkyl group which may have one or more substituents.

[0077] The catalyst can be used alone or in combination of two or more.

[0078] The amount of the catalyst used is not particularly limited. The lower limit of the amount used is, for example, 0.001 mol or more, preferably 0.005 mol or more, and more preferably 0.01 mol or more, per 1 mol of the compound represented by the formula (1). The upper limit of the amount used is, for example, 30 mol or less, preferably 20 mol or less, and more preferably 10 mol or less, per 1 mol of the compound represented by the formula (1). The amount used can be in the range of arbitrarily combining the lower limit and the upper limit.

[0079] 2-5. Solvent Step 1a is preferably carried out in the presence of a solvent. The solvent is not particularly limited, and examples thereof include the following solvents. · Hydrocarbon solvents [Examples: chain hydrocarbons such as n - hexane, aromatic hydrocarbons such as benzene, toluene, p - xylene, etc.] · Halogen - based solvents such as fluorine - based solvents and chlorine - based solvents [Examples: haloalkanes such as dichloromethane, dichloroethane, perfluorohexane; haloarenes such as chlorobenzene; haloalkylarenes such as trifluorotoluene, hexafluoromethaxylene; fluoroethers (e.g., 3M Novec 7200, 3M Novec 7300, etc. manufactured by 3M)] TM Novec TM 7200, 3M Novec TM Novec TM 7300, etc. of fluoroethers)] · Nitrile - based solvents [Examples: chain nitriles such as acetonitrile, propionitrile, acrylonitrile; cyclic nitriles such as benzonitrile] · Amide - based solvents [Examples: carboxylic acid amides (e.g., chain amides such as formamide, N - methylformamide, N,N - dimethylformamide, cyclic amides such as N - methylpyrrolidone), phosphoric acid amides (e.g., hexamethylphosphoric acid amide)] · Ether - based solvents [Examples: chain ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, cyclic ethers such as tetrahydrofuran, dioxane] · Urea - based solvents [Example: N,N - dimethylpropyleneurea] · Ester - based solvents [Example: acetate ester] · Sulfoxide - based solvents [Example: dimethyl sulfoxide] · Nitro - based solvents [Examples: nitromethane, nitrobenzene] · Ketone - based solvents [Examples: acetone, methyl ethyl ketone] · Mixed solvents of two or more of these

[0080] 2-6. Temperature The temperature of Step 1a is not particularly limited as long as the reaction proceeds. The lower limit of the temperature is, for example, -20°C or higher, preferably 0°C or higher, more preferably 10°C or higher. The upper limit of the temperature is, for example, 100°C or lower, preferably 80°C or lower, more preferably 50°C or lower. The temperature can be in the range of arbitrarily combining the lower limit and the upper limit.

[0081] 2-7. Time The time of Step 1a is not particularly limited as long as the reaction proceeds. The lower limit of the time is, for example, 3 hours or longer, preferably 6 hours or longer, more preferably 10 hours or longer. The upper limit of the time is, for example, 72 hours or shorter, preferably 50 hours or shorter. The time can be in the range of arbitrarily combining the lower limit and the upper limit.

[0082] The reaction product obtained in Step 1a may be purified by a conventional method, for example, filtration, distillation, extraction, column chromatography, etc.

[0083] 3. Method for Producing the Compound Represented by Formula (4b) In one embodiment, the method for producing the compound represented by formula (4b) includes Step 1b of allowing the compound represented by formula (1) to act on the compound represented by formula (2b) in the presence of a halogenating agent and a catalyst.

[0084] 3-1. Compound Represented by Formula (1) The compound represented by formula (1) is as described in 2-1 above.

[0085] 3-2. Compound Represented by Formula (2b) In formula (2b), each of R 2b and R 3b is preferably H, a halogen, or an alkyl group which may have a halo group as a substituent, more preferably H, a halogen, an alkyl group, or a fluoroalkyl group, even more preferably H, F, C 1-6 alkyl group, or fluoro C 1-6 alkyl group, and even more preferably H, F, C 1-4an alkyl group, or fluoro C 1-4 is an alkyl group, particularly preferably H, F, C 1-3 an alkyl group, or fluoro C 1-3 is an alkyl group. In one embodiment, (I) R 2b and R 3b are both H, (II) R 2b is H and R 3b is C 1-3 an alkyl group, or (III) R 2b and R 3b are both C 1-3 an alkyl group is preferred.

[0086] In one embodiment, R 4b is preferably an organic group. In other embodiments, R 4b is, for example, H, a halogen, or an alkyl group which may have one or more substituents, preferably a halogen, or an alkyl group which may have a halo group as a substituent, more preferably a halogen or a fluoroalkyl group, still more preferably F or a fluoroalkyl group, even more preferably F or fluoro C 1-6 an alkyl group, particularly preferably F or fluoro C 1-4 an alkyl group, particularly even more preferably F or fluoro C 1-3 an alkyl group.

[0087] X 1b may be F or a halogen other than F. In one embodiment, when R 4b is F or a fluoroalkyl group, X 1b is preferably Cl, Br, or I. Also, in one embodiment, X 1b is preferably Cl or Br.

[0088] 3-3. Halogenating Agent The halogenating agent and its amount used are as described in 2-3 above.

[0089] 3-4. Catalyst The catalyst and its amount used are as described in 2-4 above.

[0090] 3-5. Solvent Step 1b is preferably carried out in the presence of a solvent. The solvent is as described in 2-5 above.

[0091] 3-6. Temperature The temperature of Step 1b is not particularly limited as long as the reaction proceeds. The lower limit of the temperature is, for example, -20°C or higher, preferably 0°C or higher, more preferably 10°C or higher. The upper limit of the temperature is, for example, 100°C or lower, preferably 70°C or lower, more preferably 50°C or lower. The temperature can be in the range of arbitrarily combining the lower limit and the upper limit.

[0092] 3-7. Time The time of Step 1b is not particularly limited as long as the reaction proceeds. The lower limit of the time is, for example, 3 hours or longer, preferably 6 hours or longer, more preferably 10 hours or longer. The upper limit of the time is, for example, 70 hours or shorter, preferably 50 hours or shorter. The time can be in the range of arbitrarily combining the lower limit and the upper limit.

[0093] The reaction product obtained in Step 1b may be purified by a conventional method, for example, filtration, distillation, extraction, column chromatography, etc.

[0094] 4. Compound Represented by Formula (4a) The compound represented by formula (4a) is as described in 2 above.

[0095] 5. Composition Containing the Compound Represented by Formula (4b) 5-1. Compound Represented by Formula (4b) The compound represented by formula (4b) is as described in 3 above, and may be, for example, a compound represented by formula (4a). The compound represented by formula (4a) is as described in 2 above. The content of the compound represented by formula (4b) is not particularly limited, but is, for example, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more, and / or 99% by mass or less or 95% by mass or less based on 100% by mass of the composition.

[0096] 5-2. Other Components As long as the composition contains the compound represented by formula (4b), it is not particularly limited, and may further contain other components. Examples of other components include halide ions, water, the compound represented by formula (2b), a solvent, a catalyst, a carboxylic acid, a halogen adduct of the compound represented by formula (2b), the compound represented by formula (1’), Y + cations represented by, halogenating agents, oxygen, and the like. Other components can be impurities and the like in the production method of the compound represented by formula (4a) or (4b) described in 2 or 3 above. Other components may be a single species or a combination of two or more species.

[0097] 5-3. Composition Containing the Compound Represented by Formula (4b) and Halide Ions The halide ions are not particularly limited, and examples thereof include fluoride ions, chloride ions, bromide ions, and iodide ions. The halide ions are preferably chloride ions, bromide ions, or iodide ions. The halide ions can be, for example, impurities in the production method of the compound represented by formula (4a) or (4b) described in 2 or 3 above, specifically, those derived from a halogenating agent.

[0098] The content of halide ions is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 3×10 -8 % by mass or more, preferably 10 -6 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The content can be in a range obtained by arbitrarily combining the above lower limit and the above upper limit. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0099] 5-3’. Composition Containing the Compound Represented by Formula (4b), Halide Ions, and a Catalyst Examples of the halide ions include those described in 5-3 above. Examples of the catalyst include those described in 2-4 or 3-4 above. The catalyst can be, for example, derived from a catalyst that can be used in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above.

[0100] The content of halide ions is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 3×10 -8 % by mass or more, preferably 10 -6 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The content can be in a range obtained by arbitrarily combining the above lower limit and the above upper limit. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0101] The content of the catalyst is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -11 % by mass or more, preferably 10 -9 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The content can be in the range of arbitrarily combining the above lower limit and the above upper limit. The content can be measured by inductively coupled plasma mass spectrometry (IPC-MS), 1 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0102] 5-4. Composition Containing the Compound Represented by Formula (4b) and Water The content of water is not particularly limited. The upper limit of the content is, for example, 1% by mass or less, preferably 0.5% by mass or less, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -8 % by mass or more, preferably 10 -6 % by mass or more, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The content can be in the range of arbitrarily combining the above lower limit and the above upper limit. The content can be measured by the Karl Fischer method or 1 1H-NMR.

[0103] 5-4’. Composition Containing the Compound Represented by Formula (4b), Water, and a Catalyst Examples of the catalyst include those described in the above 2-4 or 3-4. The catalyst can be, for example, derived from a catalyst used in the method for producing the compound represented by the formula (4a) or (4b) described in the above 2 or 3.

[0104] The water content is not particularly limited. The upper limit of the content is, for example, 1% by mass or less, preferably 0.5% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -8 % by mass or more, preferably 10 -6 % by mass or more, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The content can be in the range of arbitrarily combining the above lower limit and the above upper limit. The content can be measured by the Karl Fischer method or 1 1H-NMR.

[0105] The content of the catalyst is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -11 % by mass or more, preferably 10 -9 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The content can be in the range of arbitrarily combining the above lower limit and the above upper limit. The content can be measured by inductively coupled plasma mass spectrometry (ICP-MS), NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0106] 5-5. Composition Containing the Compound Represented by Formula (4b) and the Compound Represented by Formula (2b) The compound represented by formula (2b) is as described in 3-2 above, and may be, for example, the compound represented by formula (2a). The compound represented by formula (2a) is as described in 2-2 above. The compound represented by formula (2b) can be, for example, an unreacted raw material in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above.

[0107] The content of the compound represented by formula (2b) is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more. The content can be in a range that arbitrarily combines the above lower limit and upper limit. The content can be measured by 1 H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0108] 5-6. Composition Containing the Compound Represented by Formula (4b) and a Solvent Examples of the solvent include those described in 2-5 or 3-5 above. The solvent can be, for example, derived from a solvent used in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above. Further, the solvent can be, for example, arbitrarily added after the production of the compound represented by formula (4b).

[0109] The content of the solvent is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more. The content can be in a range that arbitrarily combines the above lower limit and upper limit. The content can be measured by 1 H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0110] 5-7. Composition Containing the Compound Represented by Formula (4b) and a Catalyst Examples of the catalyst include those described in 2-4 or 3-4 above. The catalyst can be derived from a catalyst that can be used, for example, in the method for producing the compound represented by the formula (4a) or (4b) described in 2 or 3 above.

[0111] The content of the catalyst is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -11 % by mass or more, preferably 10 -9 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The content can be in a range obtained by arbitrarily combining the lower limit and the upper limit. The content can be measured by inductively coupled plasma mass spectrometry (IPC-MS), 1 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0112] 5-8. Composition Containing the Compound Represented by Formula (4b) and a Carboxylic Acid The carboxylic acid is not particularly limited, and examples thereof include the compound represented by the formula (6): R 1 -COOH (6) [wherein R 1 is as defined above.]. Examples of the carboxylic acid include compounds represented by the above formula (6). The carboxylic acid can be a hydrolysis product of the compound represented by the formula (1’) when the compound represented by the formula (1) is generated in the reaction system from the compound represented by the formula (1’) in the method for producing the compound represented by the formula (4a) or (4b) described in 2 or 3 above.

[0113] The content of the carboxylic acid is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The content can be in a range that arbitrarily combines the above lower limit and the above upper limit. The content can be measured by 1 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0114] 5-9. Composition Containing the Compound Represented by Formula (4b) and the Halogen Adduct of the Compound Represented by Formula (2b) The halogen adduct of the compound represented by the formula (2b) is not particularly limited. For example, the formula (7):

Chemical formula

[0115] The content of the halogen adduct is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 3×10 -9 % by mass or more, preferably 10 -6 % by mass or more, based on 100% by mass of the compound represented by the formula (4b) (or 100% by mass of the composition). The content can be in a range that arbitrarily combines the above lower limit and the above upper limit. The content can be measured by 1 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0116] 6. Method for Producing the Compound Represented by Formula (5a) The method for producing the compound represented by formula (5a) includes step 2a of allowing a reducing agent to act on the compound represented by formula (4a). It is preferable that the production method further includes step 1a.

[0117] 6-1. Compound Represented by Formula (4a) The compound represented by formula (4a) is as described in 2 above.

[0118] 6-2. Reducing Agent The reducing agent is not particularly limited as long as it can reduce the compound represented by formula (4a).

[0119] In one embodiment, the reducing agent is preferably an organometallic reagent. Examples of the organometallic reagent include Grignard reagents such as alkylmagnesium bromide like methylmagnesium bromide and ethylmagnesium bromide; and arylmagnesium bromide like phenylmagnesium bromide.

[0120] In one embodiment, the reducing agent is (i) a transition metal, an alkali metal, or an alkaline earth metal (ii) a metal pair of a transition metal, and (iii) a mixture of a transition metal and an acid or a metal salt and is preferably at least one selected from the group consisting of the above groups.

[0121] Examples of the transition metal of the reducing agent (i) include Zn, Cu, Fe, Mn, etc. Examples of the alkali metal of the reducing agent (i) include Na, etc. Examples of the alkaline earth metal of the reducing agent (i) include Mg, etc.

[0122] The metal pair of the transition metal of the reducing agent (ii) can contain the transition metals exemplified by the reducing agent (i), and examples thereof include Zn / Cu, etc.

[0123] As the mixture of reducing agent (iii), it can contain the transition metals exemplified by reducing agent (i), and examples thereof include Zn / acetic acid, Zn / ZnCl2, etc.

[0124] In one embodiment, the reducing agent is preferably a phosphorus-containing compound. Examples of the phosphorus-containing compound include triarylphosphines such as triphenylphosphine, compounds in which a plurality of phosphorus atoms such as 1,2-bis(diphenylphosphino)ethane are linked via a linker (e.g., alkylene), trialkylphosphines such as tributylphosphine, and phosphines substituted with a mixture of alkyl groups and aryl groups. Further, examples of the phosphorus-containing compound include trialkyl phosphites such as triethyl phosphite, and tri(mono- or dialkylamino)phosphines such as tri(diethylamino)phosphine.

[0125] The amount of the reducing agent used is not particularly limited. The lower limit of the amount used is, for example, 0.01 mol or more, preferably 0.1 mol or more, more preferably 0.5 mol or more, per 1 mol of the compound represented by formula (4a). The upper limit of the amount used is, for example, 10 mol or less, preferably 7 mol or less, more preferably 5 mol or less, per 1 mol of the compound represented by formula (4a). The amount used can be in the range of arbitrarily combining the above lower limit and the above upper limit.

[0126] 6-3. Solvent Step 2a is preferably carried out in the presence of a solvent. The solvent is not particularly limited, and examples thereof include the following solvents. · Hydrocarbon solvents [e.g., linear hydrocarbons such as n-hexane, and aromatic hydrocarbons such as benzene, toluene, p-xylene, etc.] · Halogenated solvents such as fluorinated solvents and chlorinated solvents [e.g., haloalkanes such as dichloromethane, dichloroethane, perfluorohexane; haloarenes such as chlorobenzene; haloalkylarenes such as trifluorotoluene, hexafluoromethaxylene; haloethers (e.g., 3M Novec 7200 manufactured by 3M Company, 3M Novec 7200 manufactured by 3M Company) TM Novec TM 7200, 3M Novec 7200 manufactured by 3M CompanyTM Novec TM such as fluoroethers like 7300) · Nitrile solvents [e.g., chain nitriles such as acetonitrile, propionitrile, acrylonitrile; cyclic nitriles such as benzonitrile] · Amide solvents [e.g., carboxylic acid amides (e.g., chain amides such as formamide, N - methylformamide, N,N - dimethylformamide; cyclic amides such as N - methylpyrrolidone), phosphoric acid amides (e.g., hexamethylphosphoric triamide)] · Ether solvents [e.g., chain ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether; cyclic ethers such as tetrahydrofuran, dioxane] · Urea solvents [e.g., N,N - dimethylpropyleneurea] · Ester solvents [e.g., acetate esters] · Sulfoxide solvents [e.g., dimethyl sulfoxide] · Nitro solvents [e.g., nitromethane, nitrobenzene] · Ketone solvents [e.g., acetone, methyl ethyl ketone] · Alcohol solvents [e.g., methanol, ethanol] · Acids [e.g., acetic acid] · Mixed solvents of two or more of these

[0127] 6-4. Temperature The temperature in Step 2a is not particularly limited as long as the reaction proceeds. The lower limit of the temperature is, for example, - 70°C or higher, preferably - 50°C or higher, more preferably - 30°C or higher. The upper limit of the temperature is, for example, 200°C or lower, preferably 150°C or lower, more preferably 100°C or lower. The temperature can be in a range that arbitrarily combines the above - mentioned lower and upper limits.

[0128] 6-5. Time The time of step 2a is not particularly limited as long as the reaction proceeds. The lower limit of the time depends on the type of reducing agent, etc., but is, for example, 5 minutes or more, preferably 10 minutes or more. The upper limit of the time is, for example, 12 hours or less, preferably 6 hours or less. The time can be in the range of arbitrarily combining the lower limit and the upper limit.

[0129] The reaction product obtained in step 2a may be purified by a conventional method, for example, filtration, distillation, extraction, column chromatography, etc.

[0130] 7. Method for Producing the Compound Represented by Formula (5b) The method for producing the compound represented by formula (5b) includes step 1b and step 2b of allowing a reducing agent to act on the compound represented by formula (4b).

[0131] 7-1. Step 1b Step 1b is as described in 3 above.

[0132] 7-2. Compound Represented by Formula (4b) The compound represented by formula (4b) is as described in 3 above.

[0133] 7-3. Reducing Agent The reducing agent and its amount used are as described in 6-2 above.

[0134] 7-4. Solvent Step 2b is preferably carried out in the presence of a solvent. The solvent is as described in 6-3 above.

[0135] 7-5. Temperature and Time The temperature and time of step 2b can be respectively selected from the same ranges as the temperature and time of step 2a described in 6-4 and 6-5 above.

[0136] The reaction product obtained in step 2b may be purified by a conventional method, for example, filtration, distillation, extraction, column chromatography, etc.

[0137] 8. Compound Represented by Formula (5c) In formula (5c), R 1c is a fluoroalkyl group having 2 or more carbon atoms or a fluoroalkoxy group having 1 or more carbon atoms, which may have one or more substituents. Examples of the substituent include a nitrile group, an ester group (e.g., R r OCO-), a formyl group, a sulfonyl-containing group (e.g., R r OSO2-), and the like. The fluoroalkyl or fluoroalkoxy group may be a perfluoroalkyl or perfluoroalkoxy group. The number of carbon atoms of the fluoroalkyl or fluoroalkoxy group is, for example, 11 or less, preferably 10 or less, more preferably 9 or less. Examples of the "heteroatom" that may be included between carbon atoms of the fluoroalkyl group or fluoroalkoxy group include, but are not limited to, an oxygen atom, a sulfur atom, a nitrogen atom, and the like.

[0138] Examples of R 1c include, for example, CF3-O- CF3-CF2- CF3-CF2-CF2- CF3-CF2-CF(CF3)- CF3-O-CF2- CF3-CF2-O- CF3-CF2-CF2-CF2- CF3-CF2-O-CF2- CF3-O-CF2-O- CF3-CF2-CF2-CF2-CF2- CF3-CF2-CF2-O-CH2- CF3-CF2-CF2-O-CF2- CF3-CF2-CF2-CF2-CF2-CF2- CF3-CF2-CF2-CF2-CF2-CF2-CF2- CF3-CF(CF3)- CF3-CF2-CF2-O-CF(CF3)- CF3-CF2-CF2-O-CF(CF3)-CF2-O-CF(CF3)- Fluoro C such as CF3-CF2-CF2-O-[CF(CF3)-CF2-O-]2-CF(CF3)- 2-11 alkyl group, fluoro C 1-3 alkoxy group, fluoro C 1-3 alkoxyfluoro C 1-3 alkoxy group, fluoro C 1-3 alkoxyfluoro C 1-3 alkoxyfluoro C 1-3 Examples include an alkoxy group and the like.

[0139] In formula (5c), R 2c and R 3c each is preferably H or a C 1-6 alkyl group, more preferably H or a C 1-4 alkyl group, still more preferably H or a C 1-3 alkyl group. In one embodiment, (I) R 2c and R 3c are both H, (II) R 2c is H and R 3c is a C 1-3 alkyl group, or (III) R 2c and R 3c are both C 1-3 alkyl groups, which is preferred.

[0140] 9. Composition Containing the Compound Represented by Formula (5b) 9-1. Compound Represented by Formula (5b) The compound represented by formula (5b) is as described in 7 above, and may be, for example, a compound represented by formula (5a) or (5c). The compounds represented by formula (5a) and (5c) are as described in 6 and 8 above, respectively. The content of the compound represented by formula (5b) is not particularly limited, but may be, for example, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more, and / or 99% by mass or less or 95% by mass or less based on 100% by mass of the composition.

[0141] 9-2. Other Components The composition is not particularly limited as long as it contains the compound represented by formula (5b), and may further contain other components. Examples of the other components include halide ions, water, the compound represented by formula (2b), a solvent, a catalyst, a carboxylic acid, a halogen adduct of the compound represented by formula (2b), the compound represented by formula (4b), a reducing agent, oxygen, and the like. The other components can be impurities and the like in the method for producing the compound represented by formula (5a) or (5b) described in 6 or 7 above. The other components may be single or in combination of two or more.

[0142] 9-3. Composition Containing the Compound Represented by Formula (5b) and Halide Ions The halide ions are not particularly limited, and examples thereof include fluoride ions, chloride ions, bromide ions, and iodide ions. The halide ions are preferably chloride ions, bromide ions, or iodide ions. Further, the halide ions can be, for example, impurities in the method for producing the compound represented by formula (5a) or (5b) described in 6 or 7 above, specifically, those derived from a halogenating agent.

[0143] The content of the halide ions is not particularly limited. The upper limit of the content is, for example, 15% by mass or less, preferably 10% by mass or less, based on 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 3×10 -8 % by mass or more, preferably 10 -6 % by mass or more, more preferably 10 -3 % by mass or more, based on 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The content can be in a range arbitrarily combining the above lower limit and the above upper limit. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0144] 9-4. Composition Containing the Compound Represented by Formula (5b) and Water The water content is not particularly limited. The upper limit of the content is, for example, 2% by mass or less, preferably 1% by mass or less, based on 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -8 % by mass or more, preferably 10 -6 % by mass or more. The content can be in the range of arbitrarily combining the above lower limit and upper limit. The content can be measured by the Karl Fischer method or 1 1H-NMR.

[0145] 9-5. Composition Containing the Compound Represented by Formula (5b) and the Compound Represented by Formula (2b) The compound represented by formula (2b) is as described in 3-2 above, and may be, for example, the compound represented by formula (2a). The compound represented by formula (2a) is as described in 2-2 above. The compound represented by formula (2b) can be, for example, derived from the raw material of step 1a or 1b described in 6 or 7 above.

[0146] The content of the compound represented by formula (2b) is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more. The content can be in the range of arbitrarily combining the above lower limit and upper limit. The content can be 1 measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0147] 9-6. Composition Containing the Compound Represented by Formula (5b) and a Solvent Examples of the solvent include those described in 2-5 or 3-5 above. The solvent can be, for example, derived from a solvent that can be used in the method for producing the compound represented by the formula (5a) or (5b) described in 6 or 7 above. Further, the solvent can be, for example, optionally added after the production of the compound represented by the formula (5b).

[0148] The content of the solvent is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by the formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more, based on 100% by mass of the compound represented by the formula (5b) (or 100% by mass of the composition). The content can be in a range obtained by arbitrarily combining the lower limit and the upper limit. The content can be 1 measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0149] 9-7. Composition Containing the Compound Represented by Formula (5b) and a Carboxylic Acid The carboxylic acid is not particularly limited, and examples thereof include the compound represented by the formula (6). The carboxylic acid can be, for example, a hydrolysis product of the compound represented by the formula (1') when the compound represented by the formula (1) is generated in the reaction system from the compound represented by the formula (1') in Step 1a or 1b described in 6 or 7 above.

[0150] The content of the carboxylic acid is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 6% by mass or less, based on 100% by mass of the compound represented by the formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6is at least the mass %. The content can be in the range of arbitrarily combining the lower limit and the upper limit. The content can be 1 measured by H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0151] 9-8. Composition Containing the Compound Represented by Formula (5b) and the Compound Represented by Formula (4b) The compound represented by formula (4b) is as described in 3 above, and for example, it may be a compound represented by formula (4a). The compound represented by formula (4a) is as described in 2 above. The compound represented by formula (4b) can be, for example, an unreacted raw material in step 2a or step 2b described in 6 or 7 above.

[0152] The content of the compound represented by formula (4b) is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the content is, for example, above the detection limit, and is, for example, 10 -9 % by mass or more, preferably 10 -6 % by mass or more. The content can be in the range of arbitrarily combining the lower limit and the upper limit. The content can be 1 measured by H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

Examples

[0153] Hereinafter, an embodiment of the present disclosure will be described in more detail by way of examples, but the present disclosure is not limited thereto.

[0154] Example 1 Synthesis of 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorohexane Under a nitrogen atmosphere, 58.1 mg of potassium fluoride (fluorinating agent) and 1 ml of triglyme were added to a 20 mL pressure-resistant container. 316 mg of perfluorohexanoyl fluoride and 0.25 ml of triglyme were added to the container. 162 mg of iodine monochloride (halogenating agent) and 0.25 ml of triglyme were added to the container. The container was cooled to 0 °C or lower, and 1.59 g of 1-chloro-1-fluoro Ethylene was added. The container was stirred at 30 °C for 18 hours. The resulting reaction mixture was dropped into a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 21%. 19 19F NMR (376 MHz, CDCl3): δ -59.9~-60.0 (m, 1F), -80.6 (t, 3F), -82.0~-85.7 (m, 2F), -121.8 (s, 2F), -122.7 (s, 2F), 125.3 (s, 2F), -125.9~-126.0 (t, 2F), 1 1H NMR (400 MHz, CDCl3): δ 3.94~3.88 (m, 2H).

[0155] The same fluoroether as in Example 1 was synthesized by operating in the same manner as the method described in Example 1 except that the types of the fluorinating agent and the halogenating agent were changed to the compounds shown in Table 1.

[0156]

Table 1

[0157] Example 9 Reaction Extension in the Synthesis of 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorohexane After carrying out the reaction in Example 1, 162 mg of iodine monochloride was further added to the container. Again, the container was cooled to 0 °C or lower, and 1.62 g of 1-chloro-1-fluoro Ethylene was added. The container was stirred at 30 °C for 18 hours. The resulting reaction mixture was dropped into a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19Analysis by FNMR showed that the title fluoroether was produced in a yield of 39%.

[0158] Example 10 Synthesis of 1-(2-bromo-1-chloro-1-fluoroethoxy)perfluorohexane Under a nitrogen atmosphere, 69.7 mg of potassium fluoride and 1 mL of triglyme were added to a 20 mL pressure-resistant container. 316 mg of perfluorohexanoyl fluoride and 1 mL of triglyme were added to the container. 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) (286 mg) and triphenylphosphine sulfide (catalyst) (29.4 mg) were added to the container. The container was cooled to 0 °C or lower, and 1.60 g of 1-chloro-1-fluoro Ethylene was added. The container was stirred at 40 °C for 18 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by FNMR showed that the title fluoroether was produced in a yield of 31%. The unreacted perfluorohexanoyl fluoride was 57%. The conversion yield considering the unreacted acid fluoride was 72%. 19 F NMR (376 MHz, CDCl3): δ -65.6~-65.7 (m, 1F), -82.4 (t, 3F), -82.8~-83.2 (m, 1F), -86.0~-86.4 (m, 1F), -123.3 (s, 2F), -124.1 (s, 2F), 126.8 (s, 2F), -127.5 (s, 2F), 1 H NMR (400 MHz, CDCl3): δ 3.95~3.91 (m, 2H).

[0159] The same fluoroether as in Example 10 was synthesized by operating in the same manner as the method described in Example 10 except that the catalyst was changed as described in Table 2.

[0160]

Table 2

[0161] Example 16 Synthesis of 1-(2-bromo-1-chloro-1-fluoroethoxy)perfluorohexane Using Bromine In a nitrogen atmosphere, 69.7 mg of potassium fluoride and 1 mL of triglyme were added to a 20 mL pressure-resistant container. 316 mg of perfluorohexanoyl fluoride and 1 mL of triglyme were added to the container. Bromine (156 mg) was added to the container. The container was cooled to 0 °C or lower, and 1.60 g of 1-chloro-1-fluoro Ethylene was added. The container was stirred at 40 °C for 18 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 43%. The obtained crude product was purified by column chromatography to obtain the title fluoroether in a yield of 40%.

[0162] The concentration of halide ions of the fluoroether obtained using ion chromatography was measured. As a result, the fluoride ion concentration was 2.1×10 -3 mass%, the chloride ion concentration was 5.3×10 -3 mass%, the bromide ion concentration was 0.4 mass%, and the iodide ion concentration was 3.7×10 -3 mass%. Also, the water concentration measured by a Karl Fischer moisture meter was 8.5×10 -2 mass%.

[0163] Example 17 Synthesis of 1-((1-fluorovinyl)oxy)perfluorohexane from 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorohexane 54.2 mg of 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorohexane (substrate) was added to a 10 mL glass container, and the inside of the container was replaced with nitrogen. 0.25 mL of diglyme (solvent) was added to the container. 35.9 mg of trisdiethylaminophosphine (reducing agent) was added to the container. Stirred at -20 °C for 1 hour, 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of over 99%. 1919F NMR (376 MHz, CDCl3): δ -81.7~-81.9 (dt, 1F), -82.9~-82.9 (t, 3F), -86.9 (br, 2F), -124.5 (s, 2F), -125.0 (s, 2F), 127.4~127.5 (t, 2F), -128.2~-128.3 (t, 2F), 1 1H NMR (400 MHz, CDCl3): δ 4.47~4.28 (m, 2H).

[0164] The reaction was carried out in the same manner as in Example 17 except that the reducing agent, solvent, substrate concentration, reaction temperature, and time were changed as shown in Table 3, and the same vinyl ether as in Example 17 was synthesized.

[0165]

Table 3

[0166] Example 27 Synthesis of 1-((1-fluorovinyl)oxy)perfluorohexane from (2-bromo-1-chloro-1-fluoroethoxy)perfluorohexane 75.8 mg of (2-bromo-1-chloro-1-fluoroethoxy) perfluorohexane was added to a 10 mL glass container, and the inside of the container was replaced with nitrogen. 0.15 mL of acetonitrile was added to the container. 49.9 mg of trisdiethylaminophosphine was added to the container. The mixture was stirred at -20 °C for 3 hours, 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 61%.

[0167] Example 28 Synthesis of 1-(2-(1-chloro-1-fluoro-2-iodoethoxy)perfluoropropoxy)perfluoropropane Under a nitrogen atmosphere, 58.1 mg of potassium fluoride and 1 ml of triglyme were added to a 20 mL pressure-resistant container. 332 mg of 2-(perfluoropropoxy) perfluoropropanoyl fluoride and 0.25 ml of triglyme were added to the container. 162 mg of iodine monochloride and 0.25 ml of triglyme were added to the container. The container was cooled to 0 °C or lower, and 1-chloro-1-fluoro Ethylene1.26 g was added. The container was stirred at 30 °C for 18 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 22%. 19 19F NMR (376 MHz, CDCl3): δ -59.4 to -59.7 (m, 1F), -79.4 to -79.5 (t, 3F), -80.4 to -80.5 (m, 2F), -81.0 (m, 3F), -85.4 to -86.4 (dd, 1F), -129.3 (s, 2F), -145.2 (s, 1F). 1 1H NMR (400 MHz, CDCl3): δ 3.92 to 3.85 (2H)

[0168] Perfluorohexane and methanol were added to the composition, and liquid separation was performed. 19 Analysis by 19F NMR showed that the title fluoroether was obtained in a yield of 19%.

[0169] 1 The concentration of water measured by 1H NMR was 5.7% by mass, and the concentration of triglyme was 2.4% by mass.

[0170] Example 29 Synthesis of 1-(2-((1-fluorovinyl)oxy)perfluoropropoxy)perfluoropropane 42.8 mg of 1-(2-(1-chloro-1-fluoro-2-iodoethoxy)perfluoropropoxy)perfluoropropane was added to a 10 mL glass container, and the inside of the container was replaced with nitrogen. 0.08 ml of acetonitrile was added to the container. 27.5 mg of tris(diethylamino)phosphine was added to the container. It was stirred at -20 °C for 1 hour, 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 65%. 19 19F NMR (376 MHz, CDCl3): δ -83.80 (br) 1 1H NMR (400 MHz, CDCl3): δ 4.46 to 4.26 (2H)

[0171] Example 30 Synthesis of 1-(1-chloro-1-fluoro-2-iodoethoxy)-3-(perfluoromethoxy)perfluoropropane Under a nitrogen atmosphere, 58.1 mg of potassium fluoride and 1 ml of triglyme were added to a 20 mL pressure-resistant container. 232 mg of 3-(perfluoromethoxy)perfluoropropanoyl fluoride and 0.25 ml of triglyme were added to the container. 162 mg of iodine monochloride and 0.25 ml of triglyme were added to the container. The container was cooled to 0 °C or lower, and 0.98 g of 1-chloro-1-fluoro Ethylene was added. The container was stirred at 30 °C for 18 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 36%. 19 19F NMR (376 MHz, CDCl3): δ -59.4~-59.5 (m, 1F) 1 1H NMR (400 MHz, CDCl3): δ 3.92~3.88 (2H).

[0172] The obtained fluoroether was 1 analyzed by 1H NMR. As a result, the obtained fluoroether contained 4.4 mass% of water and 3.6 mass% of triglyme.

[0173] Example 31 Synthesis of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 35.8 mg of 1-(1-chloro-1-fluoro-2-iodoethoxy)-3-(perfluoromethoxy)perfluoropropane was added to a 10 mL glass container, and the inside of the container was replaced with nitrogen. 0.18 ml of acetonitrile was added to the container. 28 mg of trisdiethylaminophosphine was added to the container. It was stirred at -20 °C for 1 hour, 19 Analysis by 19F NMR showed that the title fluoroether was produced in a yield of 30%. 19 19F NMR (376 MHz, CDCl3): δ -85.1~-85.2 (dt, 1F) 1 1H NMR (400 MHz, CDCl3): δ 4.46~4.24 (2H).

[0174] Example 32 Composition 1 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane To 29.6 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31, 1 ml of triglyme was added to prepare a triglyme solution containing 2.9% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane. The solution was heated at 50 °C for 2 hours, 19 and analyzed by 19F NMR. As a result, the amount of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane decreased by 2% by mass.

[0175] Example 33 Composition 2 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane To 14.8 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31, 0.5 ml of triglyme and 90 μl of water were added to prepare a triglyme solution containing 2.5% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane and 15% by mass of water. The solution was heated at 50 °C for 2 hours, 19 and analyzed by 19F NMR. As a result, the amount of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane decreased by 23% by mass.

[0176] Example 34 Composition 3 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane To 14.8 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31, 0.5 ml of triglyme, 90 μl of water, and 29 mg of potassium fluoride were added to prepare a triglyme solution containing 2.4% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane, 14% by mass of water, and 5% by mass of potassium fluoride. However, the solution separated. The solution was heated at 50 °C for 2 hours, 19When analyzed by FNMR, 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane decreased by 9% by mass.

[0177] Example 35 Composition 4 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane To 29.6 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31, 1 ml of tetrahydrofuran was added to prepare a tetrahydrofuran solution containing 3.2% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane. The solution was heated at 50 °C for 20 hours, 19 When analyzed by FNMR, 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane decreased by 16% by mass.

[0178] Example 36 Composition 5 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane To 29.6 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31, 1 ml of a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride was added to prepare a tetrahydrofuran solution containing 3.2% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane and 28% by mass of tetra-n-butylammonium fluoride. The solution was heated at 50 °C for 20 hours, 19 When analyzed by FNMR, 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane decreased by 41% by mass.

[0179] Example 35 Synthesis of 1-(1-bromo-1-fluoro-2-iodoethoxy)perfluorohexane Under a nitrogen atmosphere, 58.1 mg of potassium fluoride and 1 ml of triglyme were added to a 20 mL pressure-resistant container. 316 mg of perfluorohexanoyl fluoride and 0.25 ml of triglyme were added to the container. 162 mg of iodine monochloride and 0.25 ml of triglyme were added to the container. The container was cooled to 0 °C or lower, and 1-bromo-1-fluoroEthylene 1.48 g was added. The container was stirred at 30 °C for 18 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by FNMR showed that the title fluoroether was produced in a yield of 24%. 19 F NMR (376 MHz, CDCl3): δ -48.5~-48.6 (m, 1F), -81.9~-82.0 (m, 5F), -119.5 (t, 2F), -123.3 (s, 2F), 123.9 (s, 2F), -127.1 (t, 2F).

[0180] Example 36 Synthesis of 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorooctane Under a nitrogen atmosphere, 186 mg of tetramethylammonium fluoride and 3.5 ml of triglyme were added to a 20 mL pressure-resistant container. 832 mg of perfluorooctanoyl fluoride and 0.5 ml of triglyme were added to the container. 618 mg of N-iodosaccharin was added to the container. The container was cooled to 0 °C or below, and 1-chloro-1-fluoro Ethylene 1.37 g was added. The container was stirred at 30 °C for 24 hours. The resulting reaction mixture was added dropwise to a mixed solution of an aqueous potassium carbonate solution and an aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by FNMR showed that the title fluoroether was produced in a yield of 21%. 19 F NMR (376 MHz, CD3COCD3): δ -59.3~-59.5 (m, 1F), -81.5 (t, J = 18.4 Hz, 3F), -82.4~82.5 (m, 1F), -85.8~-86.2 (m, 1F), -121.8~-122.4 (m, 6F), -122.9~-123.2 (m, 2F), -125.9~-126.0 (m, 2F), -126.5~-126.7 (m, 2F). 1 H NMR (400 MHz, CD3COCD3): δ 4.35 (s, 1H), 4.31 (dd, J = 12.8, 16.0 Hz, 1H).

[0181] Example 37 Synthesis of 1-((1-fluorovinyl)oxy)perfluorooctane To a 10 mL glass container, 64 mg of 1-(1-chloro-1-fluoro-2-iodoethoxy)perfluorooctane was added, and the inside of the container was replaced with nitrogen. 0.25 mL of diglyme was added to the container. 35 μL of 3M phenylmagnesium bromide ether solution was added to the container. The mixture was stirred at 50 °C for 3 hours. It was added dropwise to 1M HCl, extracted with ether, 19 When analyzed by FNMR, the title fluoroether was produced in a yield of 55%. After distilling off the solvent, the title vinyl ether was obtained in 35% yield. 19 F NMR (376 MHz, CD3COCD3): δ -81.5~-81.6 (m, 1F), -81.9 (t, J = 12.0 Hz, 3F), -85.6 (t, J = 9.8 Hz, 2F), -122.4~-122.5 (m, 6F), -123.3~-123.5 (m, 2F), -126.0~-126.1 (m, 2F), -126.8~-127.0 (m, 2F). 1 H NMR (400 MHz, CDCl3): δ 4.47 (dd, J = 5.2, 6.4 Hz, 1H), 4.37 (dd, J = 4.4, 5.6 Hz, 1H).

[0182] Using ion chromatography, the concentration of halide ions in the obtained vinyl ether was measured. As a result, the chloride ion concentration was 8.7×10 -3 mass%, and the fluoride ion concentration and iodide ion concentration were below the detection limit. Also, the water concentration measured by a Karl Fischer moisture meter was 8.5×10 -2 mass%.

Claims

1. Formula (4a): 【Chemical Formula 1】 [In the formula, R １ is a fluoroalkyl group, and the fluoroalkyl group may contain an oxygen atom between carbon atoms, R ２ａ and R ３ａ are each independently H or an alkyl group, R ４ａ is F, X １ａ is a halogen other than F, X ２ is a halogen.] A method for producing a compound represented by Formula (1): 【Chemical Formula 2】 [In the formula, Y ＋ is a cation, R １ has the same meaning as defined above.] Reacting the compound represented by with a compound represented by Formula (2a): 【Chemical Formula 3】 [The symbols in the formula have the same meaning as defined above.] including Step 1a of reacting with the compound represented by wherein the halogenating agent is represented by Formula (3a): X ２ -Z (3a) [In the formula, X ２ is a halogen, Z is a halogen or NZ １ Z ２ and Z １ and Z ２ are each independently an alkyl group, an alkylcarbonyl group, an alkylsulfonyl group, Z ９ OC(=O)-(Z ９ is an alkyl group), (Z ８ )(X ２ )NC(=O)-(Z ８is an alkyl group), (Z ８ )(X ２ )NS(=O) ２ -, (Z ８ ) ２ P(=O)-, O ２ N-, (Z ８ C(=O))(X ２ )NC(=O)-, or (Z ８ S(=O) ２ )(X ２ )NC(=O)-, or Z １ and Z ２ are bonded to each other to form a ring.] Or formula (3a'): 【Chemical formula 4】 [In the formula, X ２ is halogen, Q １ ~Q ４ are each independently H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and the substituents are each independently selected from a halo group, a hydroxyl group, and a mercapto group, and any two of Q １ ~Q ４ may be bonded to each other to form a ring.] It is a compound represented by the manufacturing method.

2. Y ＋ is a metal ion or a quaternary ammonium ion, The manufacturing method of Claim 1.

3. R １ is a C １－１０ fluoroalkyl group, and the C １－１０ fluoroalkyl group may contain an oxygen atom between carbon atoms, The manufacturing method of Claim 1 or 2.

4. R ２ａ and R ３ａ are each independently H or C １－３The production method according to any one of claims 1 to 3, wherein the group is an alkyl group.

5. The production method according to any one of claims 1 to 4, wherein step 1a is carried out in the absence of a catalyst.

6. Formula (4b): 【Chemical Formula 5】 [In the formula, R １ is a fluoroalkyl group, and the fluoroalkyl group may contain an oxygen atom between carbon atoms, R ２ｂ and R ３ｂ are each independently H, a halogen, or an alkyl group, R ４ｂ is H, a halogen, a hydrocarbon group, or a fluoroalkyl group, X １ｂ and X ２ are each independently a halogen. ] A method for producing a compound represented by Formula (1): 【Chemical Formula 6】 [In the formula, Y ＋ is a cation, R １ has the same meaning as described above. ] The compound represented by is reacted with a compound represented by formula (2b): 【Chemical Formula 7】 [The symbols in the formula have the same meaning as described above. ] in step 1b, The halogenating agent is a compound represented by formula (3a): X ２ - Z (3a) [In the formula, X ２ is a halogen, Z is a halogen or NZ １ Z ２ and Z １ and Z ２is, independently of each other, an alkyl group, an alkylcarbonyl group, an alkylsulfonyl group, Z ９ OC(=O)−(Z ９ is an alkyl group), (Z ８ )(X ２ )NC(=O)−(Z ８ is an alkyl group), (Z ８ )(X ２ )NS(=O) ２ −, (Z ８ ) ２ P(=O)−, O ２ N−, (Z ８ C(=O))(X ２ )NC(=O)−, or (Z ８ S(=O) ２ )(X ２ )NC(=O)−, or Z １ and Z ２ are bonded to each other to form a ring. ] Or formula (3a'): 【Chemical formula 8】 [In the formula, X ２ is a halogen, Q １ ~Q ４ are, independently of each other, H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, the substituents being each independently selected from a halo group, a hydroxyl group, and a mercapto group, and any two of Q １ ~Q ４ may be bonded to each other to form a ring. ] is a compound represented by the production method, wherein the catalyst is a Lewis base.

7. When R ４ｂ is F or a fluoroalkyl group, X １ｂ is a halogen other than F, the production method according to claim 6.

8. Y ＋The production method according to claim 6 or 7, wherein [the ion] is a metal ion or a quaternary ammonium ion.

9. R ４ｂ The production method according to any one of claims 6 to 8, wherein R is a halogen or a fluoroalkyl group.

10. Formula (5a): 【Chemical Formula 9】 [In the formula, R １ is a fluoroalkyl group, and the fluoroalkyl group may contain an oxygen atom between carbon atoms, R ２ａ and R ３ａ are each independently H or an alkyl group, R ４ａ is F. ] A method for producing a compound represented by the formula: Formula (1): 【Chemical Formula 10】 [In the formula, Y ＋ is a cation, R １ has the same meaning as described above. ] The compound represented by the formula is reacted with a compound represented by formula (2a): 【Chemical Formula 11】 [In the formula, R ２ａ , R ３ａ , and R ４ａ have the same meaning as described above, X １ａ is a halogen other than F. ] Including step 1a of reacting with a compound represented by formula (4a): 【Chemical Formula 12】 [In the formula, R １ , R ２ａ , R ３ａ , R ４ａ , and X １ａ have the same meaning as described above, X ２ is a halogen. ] A step of producing a compound represented by, and Step 2a of allowing a reducing agent to act on the compound represented by formula (4a) comprising wherein the halogenating agent is of formula (3a): X ２ -Z (3a) [wherein, X ２ is a halogen, Z is a halogen or NZ １ Z ２ and Z １ and Z ２ are each independently an alkyl group, an alkylcarbonyl group, an alkylsulfonyl group, Z ９ OC(=O)-(Z ９ is an alkyl group), (Z ８ )(X ２ )NC(=O)-(Z ８ is an alkyl group), (Z ８ )(X ２ )NS(=O) ２ -, (Z ８ ) ２ P(=O)-, O ２ N-, (Z ８ C(=O))(X ２ )NC(=O)-, or (Z ８ S(=O) ２ )(X ２ )NC(=O)-, or Z １ and Z ２ are bonded to each other to form a ring. ] or formula (3a'): [Chemical 13] [wherein, X ２ is a halogen, Q １ ~ Q ４is, independently of each other, H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and the substituents are each independently selected from a halo group, a hydroxyl group, and a mercapto group, Q １ ~Q ４ Any two of them may be bonded to each other to form a ring. ] It is a compound represented by the following formula, and a production method thereof.

11. Formula (5b): 【Chemical Formula 14】 [In the formula, R １ is a fluoroalkyl group, and the fluoroalkyl group may contain an oxygen atom between carbon atoms, R ２ｂ and R ３ｂ are each independently H or an alkyl group, R ４ｂ is F. ] A method for producing a compound represented by the following formula, comprising Formula (1): 【Chemical Formula 15】 [In the formula, Y ＋ is a cation, R １ has the same meaning as described above. ] A compound represented by the following formula is reacted with a halogenating agent and a catalyst in the presence of a compound represented by formula (2b): 【Chemical Formula 16】 [In the formula, R ２ｂ 、R ３ｂ 、and R ４ｂ have the same meaning as described above, X １ｂ is a halogen. ] A method for producing a compound represented by formula (4b) comprising step 1b of reacting with a compound represented by the following formula: 【Chemical Formula 17】 [In the formula, R １ 、R ２ｂ , R ３ｂ , R ４ｂ , and X １ｂ have the same meaning as described above, X ２ is a halogen. ] A process for producing a compound represented by, and Step 2b of allowing a reducing agent to act on the compound represented by formula (4b) including The halogenating agent is of formula (3a): X ２ -Z (3a) [wherein, X ２ is a halogen, Z is a halogen or NZ １ Z ２ and Z １ and Z ２ are each independently an alkyl group, an alkylcarbonyl group, an alkylsulfonyl group, Z ９ OC(=O)-(Z ９ is an alkyl group), (Z ８ )(X ２ NC(=O)-(Z ８ is an alkyl group), (Z ８ )(X ２ )NS(=O) ２ -, (Z ８ ) ２ P(=O)-, O ２ N-, (Z ８ C(=O))(X ２ )NC(=O)-, or (Z ８ S(=O) ２ )(X ２ )NC(=O)-, or Z １ and Z ２ are bonded to each other to form a ring. ] or formula (3a'): [Chemical 18] [wherein, X ２ is a halogen, Q １ ~ Q ４is, independently of each other, H, an alkyl group which may have one or more substituents, a cycloalkyl group which may have one or more substituents, an aryl group which may have one or more substituents, or an aralkyl group which may have one or more substituents, and the substituents are each independently selected from a halo group, a hydroxyl group, and a mercapto group, Q １ to Q ４ Any two of them may be bonded to each other to form a ring. ] is a compound represented by a production method, wherein the catalyst is a Lewis base.

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