Haloethers and methods for producing them, and vinyl ethers and methods for producing them

Abstract

The present invention addresses the problem of providing a vinyl ether and a simple method for producing the same, as well as a haloether used in the method for producing the vinyl ether and a method for producing the same. The problem is solved by the method of formula (1): TIFF2023042598000054.tif11170[where, Y + is a cation and R 1 is an organic group.] is reacted with a compound represented by formula (2a): TIFF2023042598000055.tif21170[where, R 2a and R 3a are each independently H or an alkyl group, and R 4a is H, a halogen, or an organic group, and X 1a is a halogen other than F.].

Description

[Technical Field]

[0001] This disclosure relates to halo ethers and methods for producing the same, as well as vinyl ethers and methods for producing the same, etc. [Background technology]

[0002] Conventional methods for synthesizing fluorovinyl ethers require multiple steps. Specifically, after synthesizing a fluoroalkoxide salt by reacting an acid fluoride with a fluoride salt, fluorovinyl ethers are synthesized through 1) a substitution reaction with ethyl bromofluoroethyl acetate, 2) a reduction reaction using LiAlH4, 3) a tosylation reaction using tosyl chloride and pyridine, and 4) an elimination reaction of p-toluenesulfonic acid with lithium (bistrimethylsilyl)amide (LiHMDS) (Non-Patent Literature 1). [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Yagupolskii et al., Journal of Fluorine Chemistry, 2015, Vol. 179, pp. 134-141. [Overview of the project] [Problems that the invention aims to solve]

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

[0005] This disclosure provides vinyl ethers and a simple method for producing them, as well as halo ethers used in the method for producing vinyl ethers and methods for producing them. [Means for solving the problem]

[0006] This disclosure encompasses the following aspects: Section 1. Formula (4a): [Chemical formula] [In the formula, R , , 2 , 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 process for producing a compound represented by Formula (1): [Chemical formula] [In the formula, Y + is a cation, R 1 has the same meaning as described above.] Reacting the compound represented by with a compound represented by Formula (2a): [Chemical formula] [Symbols in the formula have the same meaning as described above.] The production process including Step 1a of reacting with the compound represented by Item 2. The halogenating agent is of 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 organic group, or Z 1 and Z 2 are bonded to each other to form a ring.] Or of Formula (3a'): [ka] [In the formula, X 2 It is a halogen, Q 1 ~Q 4 Each of these is independently either H or an organic group, and Q 1 ~Q 4 Any two of these may be joined together to form a ring. The manufacturing method described in item 1, wherein the compound is represented by [formula]. Section 3. Y + The manufacturing method according to item 1 or 2, wherein is a metal ion or a quaternary ammonium ion. Section 4. R 1 The method for producing a fluoroalkyl group according to any one of claims 1 to 3, wherein the fluoroalkyl group may have one or more substituents, and the fluoroalkyl group may contain heteroatoms between carbon atoms. Section 5. R 1 However, C may have one or more substituents. 1-10 It is a fluoroalkyl group, and the C 1-10 The manufacturing method according to any one of claims 1 to 4, wherein the fluoroalkyl group may contain a heteroatom between carbon atoms. Section 6. R 4a A manufacturing method according to any one of items 1 to 5, wherein is F or a fluoroalkyl group. Item 7. R 2a and R 3a However, each is independent of H or C 1-3 A method for producing an alkyl group as described in any one of items 1 to 6. Section 8. The manufacturing method according to any one of claims 1 to 7, wherein step 1a is carried out in the absence of a catalyst. Claim 9. Formula (4b): [ka] [In the formula, R 1 is an organic group, R2b and R 3b Each of these is independently H, a halogen, or an alkyl group which may have one or more substituents. R 4b is H, halogen, or organic group, X 1b and X 2 Each of these is an independent halogen. A method for producing a compound represented by, Formula (1): [ka] [In the formula, Y + is a cation, R 1 This is synonymous with the above. The compound represented by formula (2b) is prepared in the presence of a halogenating agent and a catalyst. [ka] [The symbols in the formula have the same meaning as above.] A method for producing a compound represented by , comprising step 1b, which involves acting on the compound represented by . Section 10. R 4b When is F or a fluoroalkyl group, X 1b The manufacturing method described in item 9, wherein is a halogen other than F. Section 11. The halogenating agent is of formula (3a): X 2 -Z (3a) [In the formula, X 2 It is a halogen, Z stands for halogen or NZ 1 Z 2 And, Z 1 and Z 2 Each of these is independently an organic group, or Z 1 and Z 2 They are joined to each other, forming a ring. Or formula (3a'): [ka] [In the formula, X 2 It is a halogen, Q 1 ~Q 4 Each of these is independently either H or an organic group, and Q 1 ~Q 4 Any two of these may be joined together to form a ring. A method of producing a compound represented by the formula described in item 9 or 10. Section 12. The manufacturing method according to any one of items 9 to 11, wherein the catalyst is a Lewis base. Section 13. The catalyst is given by formula (3b): L 1 -(Z 3 ) n (3b) [In the formula, L 1 O, N, (S) m , P, or (Se) k And, m and k are either 1 or 2. n is L 1 It is a number that corresponds to the valence of, each Z 3 Each of these is an organic group, and when n is 2 or greater, any two Z 3 They may be joined to each other to form a ring. Or formula (3c): L 2 = Z 4 (3c) [In the formula, L 2 is O, S, or Se, Z 4 is P(Z 5 )3 or C(Z 6 )2, and each Z 5 Each of these is an organic group, and any two Z 5 They may be bonded to each other to form a ring, and each Z 6 Each of these is an organic group, and any two Z 6They may be joined to each other to form a ring. A Lewis base represented by any one of items 9 to 12, a manufacturing method according to any one of the items 9 to 12. Section 14. Y + A manufacturing method according to any one of items 9 to 13, wherein is a metal ion or a quaternary ammonium ion. Section 15. R 1 The method for producing a fluoroalkyl group according to any one of claims 9 to 14, wherein the fluoroalkyl group may have one or more substituents, and the fluoroalkyl group may contain heteroatoms between carbon atoms. Section 16. R 2b and R 3b The manufacturing method according to any one of items 9 to 15, wherein each is independently H, a halogen, an alkyl group, or a fluoroalkyl group. Section 17. R 4b The manufacturing method according to any one of items 9 to 16, wherein is a halogen or a fluoroalkyl group. Section 18. Formula (4a): [ka] [In the formula, R 1 is an organic group, R 2a and R 3a Each of these is independently either H or an alkyl group. R 4a is H, halogen, or organic group, X 1a It is a halogen other than F, X 2 It is a halogen. A compound represented by the formula. Section 19. Formula (4b): [ka] [In the formula, R 1 is an organic group, R2b and R 3b is, independently of one another, H, halogen, or an alkyl group which may have one or more substituents, R 4b is H, halogen, or an organic group, X 1b and X 2 is, independently of one another, halogen.] A compound represented by the formula, and a composition containing a halide ion. Item 20. Formula (4b):

Chemical formula

Chemical formula

Advantages of the Invention

[0007] According to the present disclosure, there are provided vinyl ether and 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. Terminology Unless otherwise specifically limited, the symbols and abbreviations in this specification can be understood in the meanings 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 "containing" is used with the intention of including the terms "consisting essentially of" and "consisting of". Unless otherwise specifically limited, the processes, treatments, 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 numbers, respectively) represents, as is commonly understood by those skilled in the art, that the number of carbon atoms is n or greater 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 such "organic groups" are: A hydrocarbon group which may have one or more substituents, Alkyl molecules 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, Cyano group, 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 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 specified, examples of "alkynyl group" include linear or branched C groups such as ethynyl, 1-propyne-1-yl, 2-propyne-1-yl, 4-pentin-1-yl, and 5-hexyne-1-yl. 2-10 It can contain an alkynyl group.

[0015] In this specification, unless otherwise specified, examples of "cycloalkyl groups" include C13, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and others. 3-7 It can contain cycloalkyl groups.

[0016] In this specification, unless otherwise specified, examples of "cycloalkenyl group" include C13, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. 3-7 It can contain cycloalkenyl groups.

[0017] In this specification, unless otherwise specified, examples of "cycloalkadienyl group" include cyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cyclononadienyl, cyclodecadienyl, and other C 4-10 It can contain a cycloalkadienyl group.

[0018] In this specification, unless otherwise specified, the "aryl group" may be monocyclic, dicyclic, tricyclic, or tetracyclic. In this specification, unless otherwise specified, "aryl group" means C 6-18 It can be an aryl group. In this specification, unless otherwise specified, examples of "aryl group" may include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, and 2-anthuryl.

[0019] Unless otherwise specified herein, examples of "aralkyl group" may 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 specified, the "non-aromatic heterocyclic group" may be monocyclic, dicyclic, tricyclic, or tetracyclic. In this specification, unless otherwise specified, a "non-aromatic heterocyclic group" may be, for example, a non-aromatic heterocyclic group containing, as ring constituent atoms, 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen atoms in addition to carbon atoms. In this specification, unless otherwise specified, the "non-aromatic heterocyclic group" may be saturated or unsaturated. In this specification, unless otherwise specified, examples of "non-aromatic heterocyclic groups" include tetrahydrofuryl, oxazolidinyl, imidazolinyl (e.g., 1-imidazolinyl, 2-imidazolinyl, 4-imidazolinyl), azilidinyl (e.g., 1-azilidinyl, 2-azilidinyl), azetidinyl (e.g., 1-azetidinyl, 2-azetidinyl), and pyrrolidinyl (e.g., 1-pyro Ridinyl (2-pyrrolidinyl, 3-pyrrolidinyl), piperidinyl (e.g., 1-piperidinyl, 2-piperidinyl, 3-piperidinyl), azepanil (e.g., 1-azepanil, 2-azepanil, 3-azepanil, 4-azepanil), azocanil (e.g., 1-azepanil, 2-azepanil, 3-azepanil, 4-azepanil), piperazinyl (e.g., 1,4-piperazinyl) (e.g., 1,4-diazepine-1-yl, 1,4-piperazine-2-yl), diazepinyl (e.g., 1,4-diazepine-1-yl, 1,4-diazepine-2-yl, 1,4-diazepine-5-yl, 1,4-diazepine-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.) It can include.

[0021] In this specification, unless otherwise specified, examples of "heteroaryl groups" may include monocyclic aromatic heterocyclic groups (e.g., 5- or 6-membered monocyclic aromatic heterocyclic groups) and aromatic fused heterocyclic groups (e.g., 5- to 18-membered aromatic fused heterocyclic groups).

[0022] Unless otherwise specified herein, examples of "5 or 6-membered monocyclic aromatic heterocyclic groups" 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-pyrrolyl, 3-pyrrolyl, 4-pyrrolyl), 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) This can include thiazolyl (e.g., 2-thiazolyl, 4-thiazolyl, 5-thiazolyl), triazolyl (e.g., 1,2,3-triazole-4-yl, 1,2,4-triazole-3-yl), oxadiazolyl (e.g., 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl), thiadiazolyl (e.g., 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl), tetrazolyl, pyridyl (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl), pyridazinil (e.g., 3-pyridazinil, 4-pyridazinil), pyrimidinil (e.g., 2-pyridazinil, 4-pyridazinil, 5-pyridazinil), pyrazinil, etc.

[0023] Unless otherwise specified herein, examples of “5- to 18-membered aromatic condensed heterocyclic groups” 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), benzo[b]furanyl (e.g., 2-benzo[b]furanyl, 3-benzo[b]furanyl, 4-ben Zo[b]furanyl, 5-benzo[b]furanyl, 6-benzo[b]furanyl, 7-benzo[b]furanyl), benzo[c]furanyl (e.g., 1-benzo[c]furanyl, 4-benzo[c]furanyl, 5-benzo[c]furanyl), benzo[b]thienyl (e.g., 2-benzo[b]thienyl, 3-benzo[b]thienyl, 4-benzo[b]thienyl, 5-benzo[b]thienyl, 6-benzo[b]thienyl, 7-benzo[b]thienyl), benzo[c]thienyl (e.g., 1-benzo[c]thienyl, 4-benzo[b]thienyl) [c]thienyl, 5-benzo[c]thienyl), 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-benzoisoxazolyl (e.g., 1,2-benzoisoxazole-3-yl, 1,2-benzoisoxazole-4-yl, 1,2-benzoiso Xazol-5-yl, 1,2-benzoisoxazole-6-yl, 1,2-benzoisoxazole-7-yl), benzoxazol (e.g., 2-benzoxazol, 4-benzoxazol, 5-benzoxazol, 6-benzoxazol, 7-benzoxazol), 1,2-benzoisothiazolyl (e.g., 1,2-benzoisothiazol-3-yl, 1,2-benzoisothiazol-4-yl, 1,2-benzoisothiazol-5-yl, 1,2-benzoisothiazol-6-yl, 1,2-Benzisothiazol-7-yl), benzothiazolyl (e.g., 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7-benzothiazolyl), isoquinolil (e.g., 1-isoquinolil, 3-isoquinolil, 4-isoquinolil, 5-isoquinolil), quinolil (e.g., 2-quinolil, 3-quinolil, 4-quinolil, 5-quinolil, 8-quinolil), sinnolinyl (e.g., 3-sinnolinyl, 4-sinnolinyl, 5-sinnolinyl, 6-sin, (Nolinyl, 7-Synnorinyl, 8-Synnorinyl), 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-I) This can include 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.

[0024] In this specification, "R r Examples of "O-" include alkoxys (e.g., methoxy, ethoxy, propoxy, etc.). 1-10 Alkoxy, cycloalkoxy (e.g., cyclopentoxy, cyclohexoxy, etc.) 3-7 Cycloalkoxys, aryloxys (e.g., phenoxy, naphthoxy, etc.) 6-18 Aryloxys, and aralkyloxys (e.g., benzyloxy, phenethyloxy, etc.)7-19 It can contain aralkyloxy.

[0025] In this specification, "R r Examples of "S-" include alcoholic thio (e.g., methylthio, ethylthio, propylthio, etc.). 1-10 Alkylthio), cycloalkylthio (e.g., cyclopentylthio, cyclohexylthio, etc.) 3-7 Cycloalkylthio), arylthio (e.g., phenylthio, naphthylthio, etc.) 6-18 Aarylthio) and Aalkylthio (e.g., benzylthio, phenethylthio, etc.) 7-19 It can include Aralquilchio.

[0026] In this specification, "R r Examples of "NH-" include monoalkylaminos (e.g., monomethylamino, monoethylamino, monopropylamino, etc.). 1-10 Alkylaminos), monocycloalkylaminos (e.g., monocyclopentylaminos, monocyclohexylaminos, etc.) 3-7 Cycloalkylaminos), monoarylaminos (e.g., monophenylaminos, mononaphthylaminos, etc.) 6-18 Arylaminos, and monoaralkylaminos (e.g., monobenzylamino, monophenethylamino, etc.) 7-19 It can contain aralkylamino acids.

[0027] In this specification, "(R r Examples of ")2N-" include dialkylaminos (e.g., dimethylamino, ethylmethylamino, diethylamino, etc.) 1-10 Alkylamino), N-aryl-N-alkylamino (e.g., N-phenyl-N-methylamino, etc.) 6-18 ARY-NC 1-10 Alkylaminos, and diarylaminos (e.g., diphenylaminos, etc.) 6-18 It can contain arylaminos.

[0028] In this specification, "R rExamples of "CO-" include alkylcarbonyl [e.g., acetyl, propionyl, butyryl, etc. (C 1-10 (C)carbonyl [e.g., cyclopentanoyl, cyclohexanoyl, etc.] 3-7 (Cycloalkyl)carbonyl], arylcarbonyl [e.g., benzoyl, naphthoyl, etc.] 6-18 (C)carbonyl [e.g., benzylcarbonyl, phenethylcarbonyl, etc.] 7-19 It can contain [aralkyl (carbonyl)].

[0029] In this specification, "R r Examples of "COO-" include alkylcarbonyloxy [e.g., acetyloxy, propionyloxy, butyryloxy, etc. (C 1-10 [Alkyl)carbonyloxy], cycloalkylcarbonyloxy [Examples: cyclopentanoyl, cyclohexanoyl] (C) 3-7 (Cycloalkyl)carbonyloxy], arylcarbonyloxy [e.g., benzoyloxy, naphthoyloxy, etc. (C 6-18 (C)carbonyloxy, and aralkylcarbonyloxy [e.g., benzylcarbonyloxy, phenethylcarbonyloxy, etc.] 7-19 It can contain [aralkyl (carbonyloxy)].

[0030] In this specification, "R r Examples of "SO2-" include alkylsulfonyl (e.g., methylsulfonyl, ethylsulfonyl, propylsulfonyl, etc.) 1-10 C) (alkylsulfonyl), cycloalkylsulfonyl (e.g., cyclopentylsulfonyl, cyclohexylsulfonyl, etc.) 4-8 Cycloalkylsulfonyls), arylsulfonyls (e.g., phenylsulfonyl, naphthylsulfonyl, etc.) 6-18 Aryl sulfonyls, and aralkyl sulfonyls (e.g., benzyl sulfonyl, phenethyl sulfonyl, etc.) 7-19 It can contain aralkylsulfonyl.

[0031] In this specification, "R r Examples of "OCO-" include alkoxycarbonyls [e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc. (C 1-10 (C) alkoxycarbonyl, cycloalkoxycarbonyl [e.g., cyclopentoxycarbonyl, cyclohexoxycarbonyl, etc.] 3-7 (Cycloalkoxy)carbonyl], aryloxycarbonyl [e.g., phenoxycarbonyl, naphthoxycarbonyl, etc. (C 6-18 (C)(aryloxy)carbonyl, and aralkyloxycarbonyl [e.g., benzyloxycarbonyl, phenethyloxycarbonyl, etc.] 7-19 It can contain [aralkyloxy)carbonyl].

[0032] In this specification, "R r Examples of "OSO2-" include alkoxysulfonyl (e.g., methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, etc.) 1-10 Alkoxysulfonyls), cycloalkoxysulfonyls (e.g., cyclopentoxysulfonyl, cyclohexoxysulfonyl, etc.) 3-7 Cycloalkoxysulfonyl), aryloxysulfonyl (e.g., phenoxysulfonyl, naphthoxysulfonyl, etc.) 6-18 Aryloxysulfonyls, and aralkyloxysulfonyls (e.g., benzyloxysulfonyl, phenethyloxysulfonyl, etc.) 7-19 It can include aralkyloxysulfonyl.

[0033] In this specification, "Hydrogen groups 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", "Cycloalkyl groups 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 "substituents" in this context are, respectively, halo group, nitro group, cyano group, oxo group, thioxo group, sulfo group, sulfamoyl group, sulfinamoyl group, sulfenamoyl group, and 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 This is equivalent to the above. It can include.

[0034] Examples of the substituents referred to as "halo groups" include fluoro groups, chloro groups, bromo groups, and iodine groups.

[0035] The number of substituents can range from one 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, a method for producing the compound represented by formula (4a) includes step 1a, in which the compound represented by formula (1) is reacted with the compound represented by formula (2a) in the presence of a halogenating agent.

[0037] 2-1. Compounds represented by formula (1) In equation (1), R 1 It is not particularly limited as long as it can form oxides. 1Preferably, R is a hydrocarbon group which may have one or more substituents (the hydrocarbon group may contain heteroatoms between carbon atoms), and more preferably, an alkyl group which may have one or more substituents (the alkyl group may contain heteroatoms between carbon atoms). The "one or more substituents" that the hydrocarbon group and alkyl group may have preferably include a halo group, and more preferably include a fluoro group. That is, R 1 Preferably, is a haloalkyl group which may have one or more substituents (the haloalkyl group may contain heteroatoms between carbon atoms), and more preferably is a fluoroalkyl group which may have one or more substituents (the fluoroalkyl group may contain heteroatoms between carbon atoms). The fluoroalkyl group may be a perfluoroalkyl group. The "one or more substituents" that the haloalkyl group and fluoroalkyl group may have are a nitrile group, an ester group (e.g., R r OCO-), formyl group, sulfonyl-containing group (e.g., R r It is preferable that it contains OSO2-). Examples of heteroatoms that may be contained between the carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group include, but are not limited to, oxygen atoms, sulfur atoms, nitrogen atoms, etc. The number of carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group is not particularly limited as long as it is 1 or more, 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 above-mentioned "fluoroalkyl group which may have one or more substituents (the fluoroalkyl group may contain heteroatoms between carbon atoms)" include: 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- Fluoroc 1-10 Alkyl alkyl groups, fluorocarbon C 1-3 AlkoxyfluoroC 1-3 Alkyl alkyl groups, fluorocarbon C 1-3 AlkoxyfluoroC 1-3 AlkoxyfluoroC1-3 Alkyl alkyl groups, fluorocarbon C 1-3 AlkoxyfluoroC 1-3 AlkoxyfluoroC 1-3 AlkoxyfluoroC 1-3 Examples include alkyl groups.

[0039] In equation (1), Y + R 1 O - It is not particularly limited as long as it can be a counterion of Y. + For example, metal ions or formula (1a): [ka] [In the formula, Y 1 ~Y 4 Each of these is independently either H or an organic group, and Y 1 ~Y 4 Any two or three of these may be joined together to form a ring. This is an ion represented by formula (1a). Examples of ions represented by formula (1a) include imidazolium ion, pyridinium ion, quinolinium ion, triazinium ion, and ammonium ion.

[0040] Metal ions include monovalent and divalent metal ions, and specific examples include lithium, sodium, potassium, cesium, and silver.

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

[0042] Y 1 ~Y 4 Examples of rings formed by the bonding of any two of these elements include, but are not limited to, five- or six-membered rings such as pyrrolidine, piperidine, and morpholine.

[0043] Y + Y is a metal ion, or in formula (1a), 1 ~Y 4 It is preferable that the ion is a quaternary ammonium ion, such as an ion in which all atoms 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 metals, and more preferably lithium, sodium, potassium, cesium, or silver is suitably used.

[0044] The compound represented by formula (1) may be used directly, but also by formula (1') or formula (1''): R 1 -COF (1') R 1 -O―CH3(1'') [In the formula, R 1 This has the same meaning as above. However, in equation (1''), R 1 is R 1 '-CF2, R 1' is an organic group.' The compound represented by formula (1) may be generated in the reaction system from a compound represented by the formula shown. Specifically, the compound represented by formula (1) can be produced by reacting the compound represented by formula (1') with a fluorinating agent. That is, instead of directly using the compound represented by formula (1) as the reactant in steps 1a and 1b, the compound represented by formula (1') and a fluorinating agent can be used. The fluorinating agent is, for example, F - Y + (Y + This has the same meaning as above.) A compound represented by ), preferably an alkali metal fluoride such as potassium fluoride, rubidium fluoride, cesium fluoride, tetramethylammonium fluoride, tetraethylammonium fluoride, etc. 1-4 Alkylammonium fluorides are one example. Furthermore, the compound represented by formula (1) can be produced by reacting the compound represented by formula (1'') with an amine. That is, instead of directly using the compound represented by formula (1) as the reactant in steps 1a and 1b, the compound represented by formula (1') and the amine can be used. Examples of amines include trimethylamine, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, dimethylbenzylamine, N-methylmorpholine, tetramethylethylenediamine, and N,N'-dimethylpiperazine. For details of this method, please refer to, for example, International Publication No. 2014 / 110329.

[0045] R 1 ' is R 1 Similarly, preferably, it is a hydrocarbon group which may have one or more substituents (the hydrocarbon group may contain heteroatoms between carbon atoms), and more preferably, an alkyl group which may have one or more substituents (the alkyl group may contain heteroatoms between carbon atoms). The "one or more substituents" that the hydrocarbon group and 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 heteroatoms between carbon atoms), and more preferably a fluoroalkyl group which may have one or more substituents (the fluoroalkyl group may contain heteroatoms between carbon atoms). The fluoroalkyl group may be a perfluoroalkyl group. The "one or more substituents" that the haloalkyl group and fluoroalkyl group may have are a nitrile group, an ester group (e.g., R r OCO-), formyl group, sulfonyl-containing group (e.g., R r It is preferable that it contains OSO2-. Examples of heteroatoms that may be contained between the carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group include, but are not limited to, oxygen atoms, sulfur atoms, nitrogen atoms, etc. The number of carbon atoms of the hydrocarbon group, alkyl group, haloalkyl group, and fluoroalkyl group is not particularly limited as long as it is 1 or more, 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 compounds represented by formula (1) can be used individually or in combination of two or more.

[0047] 2-2. Compounds represented by formula (2a) In equation (2a), R 2a and R 3a Each of these is preferably H or C 1-6 It is an alkyl group, more preferably H or C 1-4 It is an alkyl group, more preferably H or C 1-3 It is an alkyl group. In one embodiment, (I)R 2a and R 3a Both are H (II)R 2a H is R 3a C 1-3 (III) Being an alkyl group R 2a and R 3a Both are C 1-3It is preferable that it be an alkyl group.

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

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

[0050] X 1a Although it is a halogen other than F, it can allow the reaction in step 1a to proceed. 1a The element is preferably Cl, Br, or I, and more preferably Cl or Br.

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

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

[0053] 2-3. Halogenating agents The halogenating agent is the R of the compound represented by formula (2a). 2a and R 3a The halogenating agent is not particularly limited, as long as it can introduce a halogen to the carbon atom it substitutes. Examples of halogenating agents include compounds represented by formula (3a) or (3a').

[0054] In equation (3a), X 2 The element is preferably Cl, Br, or I.

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

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

[0057] Z is NZ 1 Z 2 In that case, 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 or secondary amide is preferably a carboxyamide, sulfonamide, lactam, carbamate, imide, ureid, or a combination thereof. Examples of such amides 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, glycoluryl, 3a,6a-diphenylglycoluryl, 3a,6a-dimethylglycoluryl, 4,4,5,5-tetramethyl-2-imidazolidinone, and 4,4-dimethyl-2-oxazolidinone.

[0058] The primary amide is, for example, a carboxyamide. Examples of such primary carboxyamides include the following: Z such as lactam or peptide 8 C(=O)NX 2 Z 9 ; t-BuX 2 NBoc, 2-oxazolidinone derivatives (e.g., 4,4-dimethyl-2-oxazolidinone), etc. 8 NX 2 C(=O)OZ 9 (Carbamate); Z such as 2-imidazolidinone derivatives (e.g., 4,4,5,5-tetramethyl-2-imidazolidinone), glycoluryl and its derivatives (e.g., 3a,6a-diphenylglycoluryl, 3a,6a-dimethylglycoluryl) 8 NX 2 C(=O)NX 2 Z 9 (Urea derivatives) These are some examples. Furthermore, Z 8 and Z 9Each of these is an alkyl group which may have one or more substituents, and X 2 This has the same meaning as above, and refers to two X molecules present in the same molecule. 2 They may be the same or different from one another.

[0059] The primary amide is, for example, a sulfonamide, a phosphoramide, or a nitramide. An example of the sulfonamide is Z 8 S(=O)2NX 2 Z 9 , Z 8 NX 2 S(=O)2NX 2 Z 9 Examples include Z 8 2P(=O)NX 2 Z 9 Examples include O2N-NX. 2 Z 8 These are some examples. Furthermore, Z 8 , Z 9 , and X 2 This is synonymous with the above.

[0060] The aforementioned secondary amide is, for example, imide([C(=O)]2NX 2 ) is. Examples of the imide include succinimide and phthalimide. 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 (Ureido) is one example. 8 , Z 9 , and X 2 This is equivalent to the above. Non-limiting examples of ureids 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 ureid. Suitable 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, succinyl Examples include mido, phthalimide, saccharin, isocyanuric acid, 5,5-dimethylbarbituric acid, glycoluryl, 3a,6a-diphenylglycoluryl, 3a,6a-dimethylglycoluryl, 4,4,5,5-tetramethyl-2-imidazolidinone, or 4,4-dimethyl-2-oxazolidinone.

[0062] The halogenating agent is, for example, a monohalogenated or polyhalogenated amide compound.

[0063] Z is NZ 1 Z 2 Z 1 and Z 2Examples of halogenating agents in which molecules are bonded to each other to form a ring include 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-tetrahaloglycoluryl, and mixtures thereof.

[0064] In equation (3a'), Q 1 ~Q 4 It is not particularly limited as long as it can form nitrogen-containing ions. 1 ~Q 4 Each of these 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, even more preferably an alkyl group which may have one or more substituents, and particularly preferably a C which may have one or more substituents 1-4 It is an alkyl group. Examples of "substituents" that the hydrocarbon group, alkyl group, cycloalkyl group, aryl group, and aralkyl group may have include, but are not limited to, halo groups, hydroxyl groups, mercapto groups, etc.

[0065] Q 1 ~Q 4 Examples of rings formed by the bonding of any two of these elements include, but are not limited to, five- or six-membered rings such as pyrrolidine, piperidine, and morpholine.

[0066] Halogenating agents can be used individually or in combination of two or more.

[0067] The amount of halogenating agent used is not particularly limited. The lower limit of the amount used is, for example, 0.01 moles or more, preferably 0.05 moles or more, and more preferably 0.1 moles or more, per mole of the compound represented by formula (1). The upper limit of the amount used is, for example, 10 moles or less, preferably 7 moles or less, and more preferably 5 moles or less, per mole of the compound represented by formula (1). The amount used can be any combination of the lower limit and the 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 catalysts include Lewis bases. Examples of Lewis bases include compounds represented by formula (3b).

[0070] In equation (3b), L 1 O, (S) m , or (Se) k If so, then n is 2, and each Z 3 is preferably a hydrocarbon group which may have one or more substituents, and more preferably k is 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 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 "substituents" that the hydrocarbon group, alkyl group, cycloalkyl group, aryl group, and aralkyl group may have include halo groups and alkoxy groups.

[0071] L 1If is N or P, then n is 3, and each Z 3 Preferably, is 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 even 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 compounds represented by 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; trialkylamines such as triethylamine; triarylamines such as triphenylamine; trialkylphosphines such as triethylphosphine; and triarylphosphines such as triphenylphosphine.

[0073] In equation (3c), Z 4 For example, P(Z 5 )3[each Z 5 Each of these is an organic group, and any two Z 5 They may be joined to each other to form a ring. C(Z 6 )2[each Z 6 Each of these is an organic group, and the two Z 6 They may be joined to each other to form a ring. These are some examples.

[0074] each Z 5Preferably, it is 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 teeth, N(Z 7 )2[each Z 7 Each of these is an organic group, and the two Z 7 They may be joined to each other to form a ring. It is also preferable that it be so.

[0076] each Z 7 Preferably, is 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 even more preferably an alkyl group which may have one or more substituents.

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

[0078] The amount of catalyst used is not particularly limited. The lower limit of the amount used is the compound represented by formula (1). For 1 mole, the amount is, for example, 0.001 moles or more, preferably 0.005 moles or more, and more preferably 0.01 moles or more. The upper limit of the amount used is, for example, 30 moles or less, preferably 20 moles or less, and more preferably 10 moles or less, per 1 mole of the compound represented by formula (1). The amount used can be within a range that is an arbitrary combination of 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, but examples include the following solvents. • Hydrocarbon solvents [e.g., chain hydrocarbons such as n-hexane, aromatic hydrocarbons such as benzene, toluene, and p-xylene] • Halogenated solvents such as fluorinated solvents and chlorinated solvents [Examples: Haloalkanes such as dichloromethane, dichloroethane, and perfluorohexane; Haloarenes such as chlorobenzene; Haloalkylarenes such as trifluorotoluene and hexafluorometaxylene; Haloethers (Example: 3M manufactured by 3M) TM Novec TM 7200, 3M manufactured by 3M Company TM Novec TM (Fluoroethers such as 7300) • Nitrile solvents [e.g., chain nitriles such as acetonitrile, propionitrile, and acrylonitrile; cyclic nitriles such as benzonitrile] • Amide solvents [e.g., carboxylic acid amides (e.g., linear amides such as formamide, N-methylformamide, N,N-dimethylformamide, and cyclic amides such as N-methylpyrrolidone), phosphate amides (e.g., hexamethylphosphate)] • Ether-based solvents [e.g., linear ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc.] • Urea-based solvents [e.g., N,N-dimethylpropylene urea] • Ester solvents [e.g., acetate esters] • Sulfoxide-based solvents [e.g., dimethyl sulfoxide] • Nitro-based solvents [e.g., nitromethane, nitrobenzene] • Ketone solvents [e.g., acetone, methyl ethyl ketone] • A mixture of two or more of these solvents

[0080] 2-6.Temperature The temperature in 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, and more preferably 10°C or higher. The upper limit of the temperature is, for example, 100°C or lower, preferably 80°C or lower, and more preferably 50°C or lower. The temperature can be within a range that is any combination of the lower and upper limits.

[0081] 2-7.Time The duration of step 1a is not particularly limited as long as the reaction proceeds. The lower limit of this duration is, for example, 3 hours or more, preferably 6 hours or more, and more preferably 10 hours or more. The upper limit of this duration is, for example, 72 hours or less, preferably 50 hours or less. This duration can be any combination of the lower and upper limits.

[0082] The reaction product obtained in step 1a may be purified by conventional methods, such as filtration, distillation, extraction, or column chromatography.

[0083] 3. Method for producing the compound represented by formula (4b) In one embodiment, a method for producing the compound represented by formula (4b) includes step 1b, in which the compound represented by formula (1) is reacted with the compound represented by formula (2b) in the presence of a halogenating agent and a catalyst.

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

[0085] 3-2. Compounds represented by formula (2b) In equation (2b), R 2b and R 3b Each of these 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, and even more preferably H, F, C 1-6 Alkyl alkyl groups, or fluorocarbons 1-6 Alkyl alkyl groups, and more preferably H, F, C 1-4Alkyl alkyl groups, or fluorocarbons 1-4 The alkyl group is particularly preferably H, F, or C. 1-3 Alkyl alkyl groups, or fluorocarbons 1-3 It is an alkyl group. In one embodiment, (I)R 2b and R 3b (II)R 2b H is R 3b C 1-3 Being an alkyl group, or (III)R 2b and R 3b Both are C 1-3 It is preferable that it be an alkyl group. It's nice.

[0086] In one embodiment, R 4b It is preferable that it is an organic group. In another embodiment, 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, even more preferably F or a fluoroalkyl group, and even more preferably F or a fluoroC 1-6 It is an alkyl group, and particularly preferably F or fluoroC 1-4 It is an alkyl group, more preferably F or fluoroC 1-3 It is an alkyl group.

[0087] X 1b This may be F, or any other halogen. In one embodiment, R 4b When is F or a fluoroalkyl group, X 1b It is Cl, Br, or I. This is preferable. Also, in one embodiment, X 1b It is preferable that it be Cl or Br.

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

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

[0090] 3-5. Solvents 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 in 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, and more preferably 10°C or higher. The upper limit of the temperature is, for example, 100°C or lower, preferably 70°C or lower, and more preferably 50°C or lower. The temperature can be within a range that is any combination of the lower and upper limits.

[0092] 3-7.Time The duration of step 1b is not particularly limited as long as the reaction proceeds. The lower limit of this duration is, for example, 3 hours or more, preferably 6 hours or more, and more preferably 10 hours or more. The upper limit of this duration is, for example, 70 hours or less, preferably 50 hours or less. This duration can be any combination of the lower and upper limits.

[0093] The reaction product obtained in step 1b may be purified by conventional methods, such as filtration, distillation, extraction, or column chromatography.

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

[0095] 5. Compositions containing the compound represented by formula (4b) 5-1. Compounds represented by formula (4b) The compound represented by formula (4b) is as described in section 3 above, and may also be, for example, the compound represented by formula (4a). The compound represented by formula (4a) is as described in section 2 above. The content of the compound represented by formula (4b) 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.

[0096] 5-2. Other ingredients The composition is not particularly limited as long as it contains the compound represented by formula (4b), and may further contain other components. Other components include, for example, 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'), and Y + Examples include cations represented by formula (4a) or (4b), halogenating agents, and oxygen. Other components may be impurities in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above. Other components may be a single component or a combination of two or more components.

[0097] 5-3. Compositions containing a compound represented by formula (4b) and a halide ion. The halide ions are not particularly limited, but examples 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 may be, for example, impurities in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above, specifically derived from the 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 × 10⁻⁶ per 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -8 Mass% or more, preferably 10% -6 Mass% or more, more preferably 10% -3 The content is 1% by mass or more. The content can be any combination of the lower and upper limits mentioned above. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0099] 5-3'. Composition containing a compound represented by formula (4b), a halide ion, and a catalyst. Examples of halide ions include those described in 5-3 above. Examples of catalysts include those described in 2-4 or 3-4 above. The catalyst may be derived from, for example, a catalyst that can be used in a 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. For 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition), for example, 3 × 10 -8 Mass% or more, preferably 10% -6 Mass% or more, more preferably 10% -3 The content is 1% by mass or more. The content can be any combination of the lower and upper limits mentioned above. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0101] The catalyst content is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, relative to 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% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -11 Mass% or more, preferably 10% -9 Mass% or more, more preferably 10% -3 It is 1% by mass or more. The content can be any combination of the lower and upper limits. The content is determined by inductively coupled plasma mass spectrometry (IPC-MS). 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0102] 5-4. Compositions containing a compound represented by formula (4b) and water. The water content is not particularly limited. The upper limit of the water content is, for example, 1% by mass or less, preferably 0.5% by mass or less, relative to 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the water content is, for example, above the detection limit, and is, for example, 10% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -8 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is determined by the Karl Fischer method, or 1 It can be measured by 1H-NMR.

[0103] 5-4'. Composition containing a compound represented by formula (4b), water, and a catalyst. Examples of catalysts include those described in 2-4 or 3-4 above. The catalyst may be derived from a catalyst that can be used in a method for producing a compound represented by formula (4a) or (4b) as described in 2 or 3 above.

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

[0105] The catalyst content is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, relative to 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% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -11 Mass% or more, preferably 10% -9 Mass% or more, more preferably 10% -3 The content is 1% by mass or more. The content can be any combination of the lower and upper limits mentioned above. The content can be measured by inductively coupled plasma mass spectrometry (IPC-MS), NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0106] 5-5. Compositions containing a compound represented by formula (4b) and a 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) may 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, relative to 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% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0108] 5-6. Compositions containing a compound represented by formula (4b) and a solvent. Examples of solvents include those described in 2-5 or 3-5 above. The solvent may be derived from, for example, a solvent used in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above. The solvent may also be optionally added after the production of the compound represented by formula (4b), for example.

[0109] The solvent content is not particularly limited. The upper limit of the solvent content is, for example, 10% by mass or less, preferably 5% by mass or less, relative to 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). The lower limit of the solvent content is, for example, above the detection limit, and is, for example, 10% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0110] 5-7. Compositions containing a compound represented by formula (4b) and a catalyst. Examples of catalysts include those described in 2-4 or 3-4 above. The catalyst may be derived from a catalyst that can be used in a method for producing a compound represented by formula (4a) or (4b) as described in 2 or 3 above.

[0111] The catalyst content is not particularly limited. The upper limit of the content is, for example, 10% by mass or less, preferably 5% by mass or less, relative to 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% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -11 Mass% or more, preferably 10% -9 Mass% or more, more preferably 10% -3 It is 1% by mass or more. The content can be any combination of the lower and upper limits. The content is determined by inductively coupled plasma mass spectrometry (IPC-MS). 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0112] 5-8. Compositions containing a compound represented by formula (4b) and a carboxylic acid The carboxylic acid is not particularly limited, but for example, formula (6): R 1 -COOH (6) [In the formula, R 1 This is synonymous with the above. Examples include compounds represented by formula (1'). Carboxylic acids are, for example, compounds represented by formula (1') in the method for producing the compound represented by formula (4a) or (4b) described in 2 or 3 above. When the compound represented by formula (1) is generated in the reaction system, it can be a hydrolysate of the compound represented by formula (1').

[0113] The carboxylic acid content 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, 10% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0114] 5-9. Compositions containing a compound represented by formula (4b) and a halogen adduct of a compound represented by formula (2b). The halogen adduct of the compound represented by formula (2b) is not particularly limited, but for example, formula (7): [ka] [In the formula, R 2b , R 3b , R 4b , X 1b , and X 2 This is synonymous with the above. Examples include compounds represented by [the formula shown].

[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 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 × 10⁻⁶ per 100% by mass of the compound represented by formula (4b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0116] 6. Method for producing the compound represented by formula (5a) A method for producing the compound represented by formula (5a) includes step 2a, in which a reducing agent is reacted with the compound represented by formula (4a). Preferably, 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 section 2 above.

[0118] 6-2. Reducing Agents 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 organometallic reagents include Grignard reagents such as alkylmagnesium bromides like methylmagnesium bromide and ethylmagnesium bromide, and arylmagnesium bromides like phenylmagnesium bromide.

[0120] In one embodiment, the reducing agent is (i) Transition metals, alkali metals, alkaline earth metals (ii) Metal pairs of transition metals, and (iii) A mixture of a transition metal and an acid or metal salt It is preferable that it be one or more selected from the group consisting of the following:

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

[0122] The pair of transition metals for reducing agent (ii) includes the transition metals exemplified in reducing agent (i). This can be done, and examples include Zn / Cu.

[0123] The mixture of reducing agent (iii) may contain the transition metals exemplified in reducing agent (i), such as Zn / acetic acid and Zn / ZnCl2.

[0124] In one embodiment, the reducing agent is preferably a phosphorus-containing compound. Examples of phosphorus-containing compounds include triarylphosphines such as triphenylphosphine, compounds in which multiple phosphorus atoms are linked via a linker (e.g., alkylene), such as 1,2-bis(diphenylphosphine)ethane, and trialkylphosphines such as tributylphosphine. Phosphines in which alkyl and aryl groups are mixed and substituted may also be used. Furthermore, examples of phosphorus-containing compounds include trialkyl phosphites such as triethyl phosphite, and tri(diethyl Examples include tri(mono- or dialkylamino)phosphines such as amino(phosphine) and tri(mono- or dialkylamino)phosphines.

[0125] The amount of reducing agent used is not particularly limited. The lower limit of the amount used is, for example, 0.01 moles or more, preferably 0.1 moles or more, and more preferably 0.5 moles or more, per mole of the compound represented by formula (4a). The upper limit of the amount used is, for example, 10 moles or less, preferably 7 moles or less, and more preferably 5 moles or less, per mole of the compound represented by formula (4a). The amount used can be any combination of the lower limit and the upper limit.

[0126] 6-3. Solvent Step 2a is preferably carried out in the presence of a solvent. The solvent is not particularly limited, but examples include the following solvents. • Hydrocarbon solvents [e.g., chain hydrocarbons such as n-hexane, aromatic hydrocarbons such as benzene, toluene, and p-xylene] • Halogenated solvents such as fluorinated solvents and chlorinated solvents [Examples: Haloalkanes such as dichloromethane, dichloroethane, and perfluorohexane; Haloarenes such as chlorobenzene; Haloalkylarenes such as trifluorotoluene and hexafluorometaxylene; Haloethers (Example: 3M manufactured by 3M)TM Novec TM 7200, 3M manufactured by 3M Company TM Novec TM (Fluoroethers such as 7300) • Nitrile solvents [e.g., chain nitriles such as acetonitrile, propionitrile, and acrylonitrile; cyclic nitriles such as benzonitrile] • Amide solvents [e.g., carboxylic acid amides (e.g., linear amides such as formamide, N-methylformamide, N,N-dimethylformamide, and cyclic amides such as N-methylpyrrolidone), phosphate amides (e.g., hexamethylphosphate)] • Ether-based solvents [e.g., linear ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc.] • Urea-based solvents [e.g., N,N-dimethylpropylene urea] • Ester solvents [e.g., acetate esters] • Sulfoxide-based solvents [e.g., dimethyl sulfoxide] • Nitro-based solvents [e.g., nitromethane, nitrobenzene] • Ketone solvents [e.g., acetone, methyl ethyl ketone] • Alcohol-based solvents [e.g., methanol, ethanol] • Acids [e.g., acetic acid] • A mixture of two or more of these solvents

[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, and more preferably -30°C or higher. The upper limit of the temperature is, for example, 200°C or lower, preferably 150°C or lower, and more preferably 100°C or lower. The temperature can be within a range that is any combination of the lower and upper limits.

[0128] 6-5.Time The time for step 2a is not particularly limited as long as the reaction proceeds. The lower limit of this 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 this time is, for example, 12 hours or less, preferably 6 hours or less. This time can be any combination of the lower limit and the upper limit.

[0129] The reaction product obtained in step 2a may be purified by conventional methods, such as filtration, distillation, extraction, or column chromatography.

[0130] 7. Method for producing the compound represented by formula (5b) A method for producing the compound represented by formula (5b) includes step 1b and step 2b, in which a reducing agent is reacted with the compound represented by formula (4b).

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

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

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

[0134] 7-4. Solvents 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 for step 2b can be selected from the same range as the temperature and time for step 2a, as described in sections 6-4 and 6-5 above.

[0136] The reaction product obtained in step 2b may be purified by conventional methods, such as filtration, distillation, extraction, or column chromatography.

[0137] 8. Compound represented by formula (5c) In equation (5c), R 1c However, when the substituent is a fluoroalkyl group having 2 or more carbon atoms or a fluoroalkoxy group having 1 or more carbon atoms, it may have one or more substituents. Examples include nitrile groups and ester groups (e.g., R r OCO-), formyl group, sulfonyl-containing group (e.g., R r Examples include OSO2-). The fluoroalkyl or fluoroalkoxy group may be a perfluoroalkyl or perfluoroalkoxy group. The number of carbon atoms in the fluoroalkyl or fluoroalkoxy group is, for example, 11 or less, preferably 10 or less, and more preferably 9 or less. Examples of heteroatoms that may be contained between the carbon atoms of the fluoroalkyl or fluoroalkoxy group include, but are not limited to, oxygen atoms, sulfur atoms, nitrogen atoms, etc.

[0138] R 1c 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)-, Fluorococcus such as CF3-CF2-CF2-O-[CF(CF3)-CF2-O-]2-CF(CF3)- 2-11 Alkyl alkyl groups, fluorocarbon C 1-3 Alkoxy group, fluoroC 1-3 AlkoxyfluoroC 1-3 Alkoxy group, fluoroC 1-3 AlkoxyfluoroC 1-3 AlkoxyfluoroC 1-3 Examples include alkoxy groups.

[0139] In equation (5c), R 2c and R 3c Each of these is preferably H or C 1-6 It is an alkyl group, more preferably H or C 1-4 It is an alkyl group, more preferably H or C 1-3 It is an alkyl group. In one embodiment, (I)R 2c and R 3c Both are H (II)R 2c H is R 3c C 1-3 (III) Being an alkyl group R 2c and R 3c Both are C 1-3 It is preferable that it be an alkyl group.

[0140] 9. Composition containing a compound represented by formula (5b) 9-1. Compounds represented by formula (5b) The compound represented by formula (5b) is as described in 7 above, and may be, for example, the 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 ingredients The composition is not particularly limited as long as it contains the compound represented by formula (5b), and may further contain other components. Other components include, for example, halide ions, water, the compound represented by formula (2b), solvents, catalysts, carboxylic acids, and the compound represented by formula (2b). Examples include halogen adducts, compounds represented by formula (4b), reducing agents, oxygen, etc. Other components may be impurities in the method for producing the compound represented by formula (5a) or (5b) described in 6 or 7 above. Other components may be a single component or a combination of two or more components.

[0142] 9-3. Compositions containing a compound represented by formula (5b) and a halide ion. The halide ions are not particularly limited, but examples 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 may also be impurities in the method for producing the compound represented by formula (5a) or (5b) described in 6 or 7 above, specifically derived from the halogenating agent.

[0143] The content of 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 × 10⁻⁶ per 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -8 Mass% or more, preferably 10% -6 Mass% or more, more preferably 10% -3 The content is 1% by mass or more. The content can be any combination of the lower and upper limits mentioned above. The content can be measured by ion chromatography or gas chromatography-mass spectrometry (GC-MS).

[0144] 9-4. Compositions containing a compound represented by formula (5b) and water. The water content is not particularly limited. The upper limit of the water content is, for example, 2% by mass or less, preferably 1% by mass or less, relative to 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the water content is, for example, above the detection limit, and is, for example, 10% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -8 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is determined by the Karl Fischer method, or 1 It can be measured by 1H-NMR.

[0145] 9-5. Compositions containing a compound represented by formula (5b) and a 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) may be, for example, derived from the raw materials 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, relative to 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% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0147] 9-6. Compositions containing a compound represented by formula (5b) and a solvent Examples of solvents include those described in 2-5 or 3-5 above. The solvent may be derived from a solvent that can be used in the method for producing the compound represented by formula (5a) or (5b) described in 6 or 7 above. The solvent may also be, for example, represented by formula (5b) It can be optionally added after the compound has been manufactured.

[0148] The solvent content is not particularly limited. The upper limit of the solvent content is, for example, 10% by mass or less, preferably 6% by mass or less, relative to 100% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). The lower limit of the solvent content is, for example, above the detection limit, and is, for example, 10% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0149] 9-7. Compositions containing a compound represented by formula (5b) and a carboxylic acid The carboxylic acid is not particularly limited, but examples include the compound represented by formula (6). For example, in step 1a or 1b described in 6 or 7 above, when the compound represented by formula (1) is generated in the reaction system from the compound represented by formula (1'), the carboxylic acid may be a hydrolysis product of the compound represented by formula (1').

[0150] The carboxylic acid content 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% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS).

[0151] 9-8. Compositions containing a compound represented by formula (5b) and a compound represented by formula (4b) The compound represented by formula (4b) is as described in section 3 above, and may also be, for example, the compound represented by formula (4a). The compound represented by formula (4a) is as described in section 2 above. The compound represented by formula (4b) may be, for example, the unreacted raw material in step 2a or step 2b described in section 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, relative to 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% by mass of the compound represented by formula (5b) (or 100% by mass of the composition). -9 Mass% or more, preferably 10% -6 It is % by mass or more. The content can be any combination of the lower limit and the upper limit. The content is 1 It can be measured by 1H-NMR, gas chromatography (GC), or gas chromatography-mass spectrometry (GC-MS). [Examples]

[0153] One embodiment of the present disclosure will be described in more detail below by 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 triglyceride were added to a 20 mL pressure-resistant container. Perfluorohexanoyl fluoride was then added to the container. 316 mg of iodine monochloride and 0.25 ml of triglyceride were added to the container. Add 162 mg of chlorogenic acid and 0.25 ml of triglyceride to the container. Keep the container below 0°C. The mixture was cooled, and 1.59 g of 1-chloro-1-fluoroethane was added. The container was stirred at 30°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of 21%. 19 F NMR(376MHz, 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 H NMR(400MHz, CDCl3):δ 3.94~3.88(m,2H).

[0155] Except for changing the types of fluorinating and halogenating agents to the compounds shown in Table 1, the same fluoroether as in Example 1 was synthesized by following the same procedure as in Example 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 added to the container. The container was cooled again to below 0°C, and 1.62 g of 1-chloro-1-fluoroethane was added. The container was stirred at 30°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 FNMR analysis revealed that the fluoroether mentioned in the title 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 vessel. 316 mg of perfluorohexanoyl fluoride and 1 mL of triglyme were added to the same vessel. 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) (286 mg) and triphenylphosphine sulfide (catalyst) (2 9.4 mg was added. The container was cooled to below 0°C, and 1.60 g of 1-chloro-1-fluoroethane was added. The container was stirred at 40°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 FNMR analysis revealed that the fluoroether mentioned in the title was produced in a yield of 31%. Unreacted perfluorohexanoyl fluoride accounted for 57%. Considering the unreacted acid fluoride, the conversion yield was 72%. 19 F NMR(376MHz, 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 (400MHz, CDCl3): δ 3.95~3.91(m,2H).

[0159] Except for changing the catalyst as shown in Table 2, the procedure was the same as in Example 10 to synthesize the same fluoroether as in Example 10.

[0160] [Table 2]

[0161] Example 16 Synthesis of 1-(2-bromo-1-chloro-1-fluoroethoxy)perfluorohexane using bromine Under a nitrogen atmosphere, 69.7 mg of potassium fluoride and 1 mL of triglime were added to a 20 mL pressure vessel. 316 mg of perfluorohexanoyl fluoride and 1 mL of triglime were added to the vessel. Bromine (156 mg) was added to the vessel. The vessel was cooled to below 0°C, and 1.60 g of 1-chloro-1-fluoroethane was added. The vessel was stirred at 40°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis by FNMR revealed that the fluoroether described in the title was produced in 43% yield. The crude product was purified by column chromatography to obtain the fluoroether described in the title in 40% yield.

[0162] The concentration of halide ions in the fluoroether obtained using ion chromatography was measured. As a result, the fluoride ion concentration was 2.1 × 10⁻⁶. -3 The chloride ion concentration is 5.3 × 10⁻¹⁶ by mass. -3 The mass percentage is 0.4 mass%, the bromide ion concentration is 0.4 mass%, and the iodide ion concentration is 3.7 × 10⁻⁶. -3 The concentration was measured in mass percent. Furthermore, the water concentration measured using a Karl Fischer moisture meter was 8.5 × 10⁻⁶. -2 It was in mass percent.

[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 container was purged 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. The mixture was stirred at -20°C for 1 hour. 19 Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of over 99%. 19 F NMR(376MHz, CDCl3):δ -81.7~-81.9(dt, 1 F),-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 H NMR(400MHz, CDCl3):δ 4.47~4.28(m,2H).

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

[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 container was purged 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 using FNMR revealed that the fluoroether mentioned in the title 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 triglim were added to a 20 mL pressure vessel. 332 mg of 2-(perfluoropropoxy)perfluoropropanoyl fluoride and 0.25 ml of triglim were added to the same vessel. 162 mg of iodine monochloride and 0.25 ml of triglim were added to the same vessel. The vessel was cooled to below 0°C, and 1.26 g of 1-chloro-1-fluoroethane was added. The vessel was stirred at 30°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of 22%. 19 F NMR(376MHz, CDCl3):δ -59.4~-59.7(m, 1F ),-79.4~-79.5(t, 3F),-80.4~-80.5(m, 2F),-81.0(m, 3F),-85.4~-86.4(dd, 1F),-129.3(s, 2F),-145.2(s, 1F). 1 H NMR(400MHz, CDCl3):δ 3.92~3.85(2H)

[0168] Perfluorohexane and methanol were added to the compositional material, and liquid-liquid separation was performed. 19 Analysis by FNMR revealed that the fluoroether mentioned in the title was obtained in a yield of 19%.

[0169] 1 The water concentration measured by 1H NMR was 5.7% by mass, and the triglim concentration 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 container was purged with nitrogen. 0.08 ml of acetonitrile was added to the container. 27.5 mg of trisdiethylaminophosphine was added to the container. The mixture was stirred at -20°C for 1 hour. 19 Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of 65%. 19 F NMR(376MHz, CDCl3):δ -83.80(br) 1 H NMR(400MHz, CDCl3):δ 4.46~4.26(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 triglim were added to a 20 mL pressure vessel. 232 mg of 3-(perfluoromethoxy)perfluoropropanoyl fluoride and 0.25 ml of triglim were added to the same vessel. 162 mg of iodine monochloride and 0.25 ml of triglim were added to the same vessel. The vessel was cooled to below 0°C, and 0.98 g of 1-chloro-1-fluoroethane was added. The vessel was stirred at 30°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 FNMR analysis revealed that the fluoroether mentioned in the title was produced in a yield of 36%. 19 F NMR(376MHz, CDCl3):δ -59.4~-59.5(m, 1F ) 1 H NMR(400MHz, CDCl3):δ 3.92~3.88(2H).

[0172] The obtained fluoroether 1 Analysis was performed by 1H NMR. The results showed that the obtained fluoroether contained 4.4% by mass of water and 3.6% by mass of triglime.

[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 container was purged with nitrogen. 0.18 ml of acetonitrile was added to the container. 28 mg of trisdiethylaminophosphine was added to the container. The mixture was stirred at -20°C for 1 hour. 19 FNMR analysis revealed that the fluoroether mentioned in the title was produced in a yield of 30%. 19 F NMR(376MHz, CDCl3):δ -85.1~-85.2(dt, 1 F) 1H NMR(400MHz, CDCl3):δ 4.46~4.24(2H).

[0174] Example 32 Composition 1 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 29.6 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31 was added to 1 ml of triglyme to prepare a triglyme solution containing 2.9% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane. This solution was heated at 50°C for 2 hours. 19 FNMR analysis revealed a 2% decrease in 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane by mass.

[0175] Example 33 Composition 2 of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 14.8 mg of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane obtained in Example 31 was mixed with 0.5 ml of triglyme and 90 μl of water to prepare a triglyme solution containing 2.5% by mass of 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane and 15% by mass of water. This solution was heated at 50°C for 2 hours. 19 Analysis by FNMR revealed a 23% decrease in 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 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. The solution separated. The solution was heated at 50°C for 2 hours. 19FNMR analysis revealed a 9% decrease in 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 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. This solution was heated at 50°C for 20 hours. 19 Analysis by FNMR revealed a 16% decrease in 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 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 1 M 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. This solution was heated at 50°C for 20 hours. 19 Analysis by FNMR revealed a 41% decrease in 1-((1-fluorovinyl)oxy)-3-(perfluoromethoxy)perfluoropropane 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 triglim were added to a 20 mL pressure vessel. 316 mg of perfluorohexanoyl fluoride and 0.25 ml of triglim were added to the same vessel. 162 mg of iodine monochloride and 0.25 ml of triglim were added to the same vessel. The vessel was cooled to below 0°C, and 1.48 g of 1-bromo-1-fluoroethane was added. The vessel was stirred at 30°C for 18 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of 24%. 19 F NMR(376MHz, 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 then added to the container. N-yaw was added to the container. 618 mg of saccharin was added. The container was cooled to below 0°C, and 1.37 g of 1-chloro-1-fluoroethane was added. The container was stirred at 30°C for 24 hours. The resulting reaction mixture was added dropwise to a mixture of aqueous potassium carbonate solution and aqueous sodium sulfite solution, and extracted with ethyl acetate. 19 Analysis using FNMR revealed that the fluoroether mentioned in the title was produced in a yield of 21%. 19 F NMR(376MHz, CD3COCD3):δ -59.3~-59.5(m , 1F),-81.5(t,J = 18.4Hz,3F),-82.4~82.5(m,1F),-85.8~-86.2(m,1F),-121.8~-122.4(m,6 F),-122.9~-123.2(m,2F),-125.9~-126.0(m,2F),-126.5~-126.7(m,2F). 1 H NMR (400MHz, CD3COCD3): δ 4.35(s, 1H), 4.3 1 (dd, J=12.8, 16.0Hz, 1H).

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

[0182] The concentration of halide ions in the obtained vinyl ether was measured using ion chromatography. As a result, the chloride ion concentration was 8.7 × 10⁻⁶. -3The mass percentage, fluoride ion concentration, and iodide ion concentration were below the detection limit. Furthermore, the water concentration measured by the Karl Fischer moisture meter was 8.5 × 10⁻⁶. -2 It was in mass percent.

Claims

1. Formula (5a): 【Chemistry 1】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom 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 following formula: Formula (4a): 【Chemistry 2】 [In the formula, R 1 , R 2a , R 3a , and R 4a are as defined above; X 1a is a halogen other than F; X 2 is a halogen. The production method includes a step 2a of reacting a compound represented by the following formula (1):

2. The method according to claim 1, wherein R 1 is a C 1-10 fluoroalkyl group optionally having one or more substituents, and said C 1-10 fluoroalkyl group may contain a heteroatom between the carbon atoms.

3. A method for producing a compound according to claim 1 or 2, wherein the reducing agent is an organometallic reagent.

4. The reducing agent is (i) Transition metals, alkali metals, alkaline earth metals (ii) a metal pair of a transition metal, and (iii) A mixture of a transition metal with an acid or a metal salt. The method according to claim 1 or 2, wherein the compound is one or more selected from the group consisting of:

5. A method for producing a composition according to claim 1 or 2, wherein the reducing agent is a phosphorus-containing compound.

6. Formula (5c): 【Chemistry 3】 [In the formula, 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, and the fluoroalkyl or fluoroalkoxy group may contain a heteroatom between the carbon atoms; R 2c and R 3c are each independently H or an alkyl group; R 4c is F. A compound represented by the formula:

7. Formula (5b): 【Chemistry 4】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom between carbon atoms; R 2b and R 3b are each independently H or an alkyl group; R 4b is F.] A composition comprising a compound represented by the formula: and a halide ion, The content of the halide ion as measured by ion chromatography is 8.7×10 −3 mass % or less relative to 100 mass % of the composition.

8. Formula (5b): 【Chemistry 5】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom between carbon atoms; R 2b and R 3b are each independently H or an alkyl group, and R 4b is F. and water, wherein the content of water as measured by the Karl Fischer method is 8.5×10 −2 mass % or less relative to 100 mass % of the composition.

9. Formula (4a): 【Chemistry 6】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom 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 compound represented by the formula:

10. Formula (4b): 【Chemistry 7】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom between carbon atoms; R 2b and R 3b each independently represent H, a halogen, or an alkyl group which may have one or more substituents; R 4b is H, a halogen, or a hydrocarbon group which may have one or more substituents, and X 1b and X 2 are each independently a halogen.] A composition comprising a compound represented by the formula: and a halide ion, The content of the halide ion as measured by ion chromatography is 0.4111% by mass or less, based on 100% by mass of the composition.

11. Formula (4b): 【Chemistry 8】 [In the formula, R 1 is a fluoroalkyl group which may have one or more substituents, and the fluoroalkyl group may contain a heteroatom between carbon atoms; R 2b and R 3b each independently represent H, a halogen, or an alkyl group which may have one or more substituents; R 4b is H, a halogen, or a hydrocarbon group which may have one or more substituents, and X 1b and X 2 are each independently a halogen.] A composition comprising a compound represented by the formula: The composition has a water content, as measured by the Karl Fischer method, of 8.5×10 −2 % by mass or less, based on 100% by mass of the composition.

12. The composition according to claim 10 or 11, wherein when R 4b is F or a fluoroalkyl group, X 1b is a halogen other than F.

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