Process for producing a fluorinated organic compound

Abstract

A novel method for producing a fluorinated organic compound is provided. The method for producing a fluorinated organic compound comprises a step in which a compound represented by formula (1) (wherein R1 and R2 are each independently a hydrogen atom, a halogen atom, or an organic group or may have formed a ring in cooperation with two carbon atoms adjacent thereto, n is 1 or 2, and the two R1 moieties may be the same or different and the two R2 moieties may be the same or different or the two R1 moieties or the two R2 moieties may have formed a ring in cooperation with carbon atom adjacent thereto) is reacted with (A) at least one fluorine source selected from the group consisting of hydrogen fluoride, hydrogen fluoride salts, and fluoride salts and (B) a source of a halogen other than fluorine which is represented by the formula R3(OX)m (wherein R3 is a hydrogen atom, a cation, or an organic group, X is a halogen atom which is not a fluorine atom, and m is an integer corresponding to the valence of R3), thereby causing both a fluorine atom and a non-fluorine halogen atom to be added to the double bond or triple bond.

Description

Technical Field

[0001] The present disclosure relates to a method for producing a fluorinated organic compound.

Background Art

[0002] Fluorinated organic compounds are extremely important compounds as various chemical products such as functional materials, pharmaceutical and agricultural compounds, electronic materials, and their intermediates.

[0003] As a method for producing a fluorinated organic compound, for example, Non-Patent Document 1 describes a method of reacting an alkene with a hypohalite and BF3 in a non-polar solvent such as CH2Cl2 or CCl4. Further, Non-Patent Document 2 describes a method of reacting an alkene with hydrogen fluoride pyridine and N-halosuccinimide.

Prior Art Documents

Non-Patent Documents

[0004]

Non-Patent Document 1

Non-Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] BF3 in Non-Patent Document 1 and N-halosuccinimide in Non-Patent Document 2 are expensive, and there is room for improvement in terms of production cost.

[0006] An object of the present disclosure is to provide a novel method for producing a fluorinated organic compound.

Means for Solving the Problems

[0007] This disclosure includes the following aspects. Item 1. Formula (1):

Chemical formula

Chemical formula

Chemical formula

Advantages of the Invention

[0008] According to the present disclosure, a novel production method of a fluorinated organic compound is provided.

Embodiments for Carrying Out the Invention

[0009] The above summary of the present disclosure is not intended to describe each disclosed embodiment or all implementations of the present disclosure.

[0010] The following description of the present disclosure more specifically exemplifies the exemplary embodiments.

[0011] In some places of the present disclosure, guidance is provided through exemplification, and this exemplification can be used in various combinations.

[0012] In each case, the exemplary group can function as a non-exclusive and representative group.

[0013] All publications, patents, and patent applications cited in this specification are hereby incorporated by reference in their entirety.

[0014] [Terms] The symbols and abbreviations in this specification can be understood to have the meanings commonly used in the technical field to which this disclosure pertains, in accordance with the context of this specification, unless otherwise specifically limited.

[0015] In this specification, the phrase "comprising" is intended to be used to include the phrases "consisting essentially of" and "consisting of".

[0016] Unless otherwise specifically limited, the processes, treatments, or operations described in this specification can be carried out at room temperature.

[0017] In this specification, room temperature can be understood to mean a temperature within the range of 10 to 40 °C.

[0018] In this specification, the notation "C n- C m " (where n and m are each an integer of 1 or more) represents, as is commonly understood by those skilled in the art, that the number of carbon atoms is n or more and m or less.

[0019] In this specification, the phrase "compound represented by formula (N)" (where N is an integer of 1 or more) can be referred to as compound (N).

[0020] In this specification, unless otherwise specifically limited, examples of the "halogen atom" can include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0021] In this specification, the "organic group" means a group containing one or more carbon atoms. Examples of the said "organic group" are an alkyl group which may have one or more substituents, an alkenyl group which may have one or more substituents, an alkynyl group which may have one or more substituents, A cycloalkyl group which may have one or more substituents, A cycloalkenyl group which may have one or more substituents, A cycloalkadienyl group which may have one or more substituents, An aryl group which may have one or more substituents, An aralkyl group which may have one or more substituents, A non-aromatic heterocyclic group which may have one or more substituents, A heteroaryl group which may have one or more substituents, A cyano group, An aldehyde group, A carboxyl group, R r O−, R r CO−, R r COO−, R r SO2−, R r OCO−, and R r OSO2− (In these formulas, R r is independently An alkyl group which may have one or more substituents, An alkenyl group which may have one or more substituents, An alkynyl group which may have one or more substituents, A cycloalkyl group which may have one or more substituents, A cycloalkenyl group which may have one or more substituents, A cycloalkadienyl group which may have one or more substituents, An aryl group which may have one or more substituents, An aralkyl group which may have one or more substituents, A non-aromatic heterocyclic group which may have one or more substituents, or A heteroaryl group which may have one or more substituents.) can be included.

[0022] In this 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 groups that are combinations thereof.

[0023] In this specification, unless otherwise particularly limited, examples of the "alkyl group" can include linear or branched C1-16 alkyl groups (e.g., C1-C14 alkyl groups, C1-C12 alkyl groups) such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0024] In this specification, unless otherwise particularly limited, examples of the "alkenyl group" can include linear or branched C2-C10 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.

[0025] In this specification, unless otherwise particularly limited, examples of the "alkynyl group" can include linear or branched C2-C10 alkynyl groups such as ethynyl, 1-propyn-1-yl, 2-propyn-1-yl, 4-pentyn-1-yl, and 5-hexyn-1-yl.

[0026] In this specification, unless otherwise particularly limited, examples of the "cycloalkyl group" can include C3-C7 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.

[0027] In this specification, unless otherwise particularly limited, examples of the "cycloalkenyl group" can include C3-C7 cycloalkenyl groups such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl.

[0028] In this specification, unless otherwise particularly limited, examples of the "cycloalkadienyl group" can include C4-C10 cycloalkadienyl groups such as cyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cyclononadienyl, cyclodecadienyl, etc.

[0029] In this specification, unless otherwise particularly limited, the "aryl group" can be monocyclic, bicyclic, tricyclic, or tetracyclic.

[0030] In this specification, unless otherwise particularly limited, the "aryl group" can be a C6-C18 aryl group.

[0031] In this specification, unless otherwise particularly limited, examples of the "aryl group" can include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, and 2-anthryl.

[0032] In this specification, unless otherwise particularly limited, examples of the "aralkyl group" can include benzyl, phenethyl, diphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, 2,2-diphenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 2-biphenylylmethyl, 3-biphenylylmethyl, and 4-biphenylylmethyl.

[0033] In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be monocyclic, bicyclic, tricyclic, or tetracyclic.

[0034] In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be, for example, a non-aromatic heterocyclic group containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms in addition to carbon atoms as ring-constituting atoms.

[0035] In this specification, unless otherwise particularly limited, the "non-aromatic heterocyclic group" can be saturated or unsaturated.

[0036] In this specification, unless otherwise particularly limited, examples of the "non-aromatic heterocyclic group" include tetrahydrofuryl, oxazolidinyl, imidazolinyl (e.g., 1-imidazolinyl, 2-imidazolinyl, 4-imidazolinyl), aziridinyl (e.g., 1-aziridinyl, 2-aziridinyl), azetidinyl (e.g., 1-azetidinyl, 2-azetidinyl), pyrrolidinyl (e.g., 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl), piperidinyl (e.g., 1-piperidinyl, 2-piperidinyl, 3-piperidinyl), azepanyl (e.g., 1-azepanyl, 2-azepanyl, 3-azepanyl, 4-azepanyl), azocanyl (e.g., 1-azocanyl, 2-azocanyl, 3-azocanyl, 4-azocanyl), piperazinyl (e.g., 1,4-piperazin-1-yl, 1,4-piperazin-2-yl), diazepinyl (e.g., 1,4-diazepin-1-yl, 1,4-diazepin-2-yl, 1,4-diazepin-5-yl, 1,4-diazepin-6-yl), diazocanyl (e.g., 1,4-diazocan-1-yl, 1,4-diazocan-2-yl, 1,4-diazocan-5-yl, 1,4-diazocan-6-yl, 1,5-diazocan-1-yl, 1,5-diazocan-2-yl, 1,5-diazocan-3-yl), tetrahydropyranyl (e.g., tetrahydropyran-4-yl), morpholinyl (e.g., 4-morpholinyl), thiomorpholinyl (e.g., 4-thiomorpholinyl), 2-oxazolidinyl, dihydrofuryl, dihydropyranyl, and dihydroquinolyl, etc.

[0037] In this specification, unless otherwise particularly limited, examples of the "heteroaryl group" can include monocyclic aromatic heterocyclic groups (e.g., 5- or 6-membered monocyclic aromatic heterocyclic groups) and aromatic condensed heterocyclic groups (e.g., 5- to 18-membered aromatic condensed heterocyclic groups).

[0038] In this specification, unless otherwise specifically limited, examples of the "5- or 6-membered monocyclic aromatic heterocyclic group" include pyrrolyl (e.g., 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl), furyl (e.g., 2-furyl, 3-furyl), thienyl (e.g., 2-thienyl, 3-thienyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl), imidazolyl (e.g., 1-imidazolyl, 2-imidazolyl, 4-imidazolyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl), thiazolyl (e.g., 2-thiazolyl, 4-thiazolyl, 5-thiazolyl), triazolyl (e.g., 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl), oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl), thiadiazolyl (e.g., 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl), tetrazolyl, pyridyl (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl), pyridazinyl (e.g., 3-pyridazinyl, 4-pyridazinyl), pyrimidinyl (e.g., 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl), pyrazinyl, etc.

[0039] In this specification, unless otherwise specifically limited, examples of the "5- to 18-membered aromatic condensed heterocyclic group" include isoindolyl (e.g., 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl), indolyl (e.g., 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl), benzo[b]furanyl (e.g., 2-benzo[b]furanyl, 3-benzo[b]furanyl, 4-benzo[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[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-benzisoxazolyl (e.g., 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl), benzoxazolyl (e.g., 2-benzoxazolyl, 4-benzoxazolyl, 5-benzoxazolyl, 6-benzoxazolyl, 7-benzoxazolyl), 1,2-benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,(2-benzisothiazol-7-yl), benzothiazolyl (e.g., 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7-benzothiazolyl), isoquinolyl (e.g., 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl), quinolyl (e.g., 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 8-quinolyl), cinnolinyl (e.g., 3-cinnolinyl, 4-cinnolinyl, 5-cinnolinyl, 6-cinnolinyl, 7-cinnolinyl, 8-cinnolinyl), phthalazinyl (e.g., 1-phthalazinyl, 4-phthalazinyl, 5-phthalazinyl, 6-phthalazinyl, 7-phthalazinyl, 8-phthalazinyl), quinazolinyl (e.g., 2-quinazolinyl, 4-quinazolinyl, 5-quinazolinyl, 6-quinazolinyl, 7-quinazolinyl, 8-quinazolinyl), quinoxalinyl (e.g., 2-quinoxalinyl, 3-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 7-quinoxalinyl, 8-quinoxalinyl), pyrazolo[1,5-a]pyridyl (e.g., pyrazolo[1,5-a]pyridin-2-yl, pyrazolo[1,5-a]pyridin-3-yl, pyrazolo[1,5-a]pyridin-4-yl, pyrazolo[1,5-a]pyridin-5-yl, pyrazolo[1,5-a]pyridin-6-yl, pyrazolo[1,5-a]pyridin-7-yl), imidazo[1,2-a]pyridyl (e.g., imidazo[1,2-a]pyridin-2-yl, imidazo[1,2-a]pyridin-3-yl, imidazo[1,2-a]pyridin-5-yl, imidazo[1,2-a]pyridin-6-yl, imidazo[1,2-a]pyridin-7-yl, imidazo[1,2-a]pyridin-8-yl), etc. can be included.,

[0040] In this specification, "R r Examples of "O-" can include alkoxy (e.g., C1-C10 alkoxy such as methoxy, ethoxy, propoxy, butoxy, etc.), cycloalkoxy (e.g., C3-C7 cycloalkoxy such as cyclopentoxy, cyclohexoxy, etc.), aryloxy (e.g., C6-C18 aryloxy such as phenoxy, naphthoxy, etc.), and aralkyloxy (e.g., C7-C19 aralkyloxy such as benzyloxy, phenethyloxy, etc.).

[0041] In this specification, examples of "R r CO-" can include alkylcarbonyl [(C1-C10 alkyl)carbonyl such as acetyl, propionyl, butyryl, etc.], cycloalkylcarbonyl [(C3-C7 cycloalkyl)carbonyl such as cyclopentanoyl, cyclohexanoyl, etc.], arylcarbonyl [(C6-C18 aryl)carbonyl such as benzoyl, naphthoyl, etc.], and aralkylcarbonyl [(C7-C19 aralkyl)carbonyl such as benzylcarbonyl, phenethylcarbonyl, etc.].

[0042] In this specification, examples of "R r COO-" can include alkylcarbonyloxy [(C1-C10 alkyl)carbonyloxy such as acetyloxy, propionyloxy, butyryloxy, etc.], cycloalkylcarbonyloxy [(C3-C7 cycloalkyl)carbonyloxy such as cyclopentanoyloxy, cyclohexanoyloxy, etc.], arylcarbonyloxy [(C6-C18 aryl)carbonyloxy such as benzoyloxy, naphthoyloxy, etc.], and aralkylcarbonyloxy [(C7-C19 aralkyl)carbonyloxy such as benzylcarbonyloxy, phenethylcarbonyloxy, etc.].

[0043] In this specification, examples of "R r SO2-" can include alkylsulfonyl (C1-C10 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, etc.), cycloalkylsulfonyl (C4-C8 cycloalkylsulfonyl such as cyclopentylsulfonyl, cyclohexylsulfonyl, etc.), arylsulfonyl (C6-C18 arylsulfonyl such as phenylsulfonyl, naphthylsulfonyl, etc.), and aralkylsulfonyl (C7-C19 aralkylsulfonyl such as benzylsulfonyl, phenethylsulfonyl, etc.).

[0044] In this specification, "R rExamples of "OCO-" include alkoxycarbonyl [e.g., (C1-C10 alkoxy)carbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc.], cycloalkoxycarbonyl [e.g., (C3-C7 cycloalkoxy)carbonyl such as cyclopentoxycarbonyl, cyclohexoxycarbonyl, etc.], aryloxycarbonyl [e.g., (C6-C18 aryloxy)carbonyl such as phenoxycarbonyl, naphthoxycarbonyl, etc.], and aralkyloxycarbonyl [e.g., (C7-C19 aralkyloxy)carbonyl such as benzyloxycarbonyl, phenethyloxycarbonyl, etc.].

[0045] In this specification, "R r Examples of "OSO2-" include alkoxysulfonyl (e.g., C1-C10 alkoxysulfonyl such as methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, etc.), cycloalkoxysulfonyl (e.g., C3-C7 cycloalkoxysulfonyl such as cyclopentoxysulfonyl, cyclohexoxysulfonyl, etc.), aryloxysulfonyl (e.g., C6-C18 aryloxysulfonyl such as phenoxysulfonyl, naphthoxysulfonyl, etc.), and aralkyloxysulfonyl (e.g., C7-C19 aralkyloxysulfonyl such as benzyloxysulfonyl, phenethyloxysulfonyl, etc.).

[0046] In this specification, "a hydrocarbon group which may have one or more substituents", "an alkyl group which may have one or more substituents", "an alkenyl group which may have one or more substituents", "an alkynyl group which may have one or more substituents", "a cycloalkyl group which may have one or more substituents", "a cycloalkenyl group which may have one or more substituents", "a cycloalkadienyl group which may have one or more substituents", "an aryl group which may have one or more substituents", "an aralkyl group which may have one or more substituents", "a non-aromatic heterocyclic group which may have one or more substituents", and "a heteroaryl group which may have one or more substituents" Examples of the "substituent" in each of them include a halo group, a nitro group, a cyano group, an oxo group, a thioxo group, a carboxyl group, a sulfo group, a sulfamoyl group, a sulfinamoyl group, a sulfenamoyl group, R r O-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R r OSO2- (in these formulas, R r is as defined above.) can be included.

[0047] Among the substituents, examples of the "halo group" can include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0048] The number of the substituents can be within the range from 1 to the maximum number that can be substituted (e.g., 1, 2, 3, 4, 5, 6).

[0049] [Method for producing a halogen adduct of compound (1)] The production method of the present disclosure includes a step of reacting compound (1) with a fluorine source (A) and a halogen source (B) other than fluorine to add fluorine and a halogen other than fluorine to the double bond or triple bond of compound (1).

[0050] Reaction substrate: Compound (1) In one embodiment of compound (1), preferably, R 1 and R 2is, independently, a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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, More preferably, R 1 and R 2 are, independently, a hydrogen atom, a halogen atom, an alkyl group which may be substituted with one or more halo groups, an alkoxy group which may be substituted with one or more halo groups, an alkoxyalkyl group which may be substituted with one or more halo groups, an alkylcarbonyl group which may be substituted with one or more halo groups, an alkylcarbonyloxy group which may be substituted with one or more halo groups, an alkoxycarbonyl group which may be substituted with one or more halo groups, 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.

[0051] The substituent can be any group having a structure capable of substitution on the target, and for example, can be at least one selected from the group consisting of a halo group, a hydroxyl group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyl group, an arylcarbonyloxy group, an aryloxycarbonyl group, and an aryl group. The number of the substituents can be selected from within the range from 1 to the maximum number capable of substitution (e.g., 1, 2, 3).

[0052] In one embodiment, R 1 and R 2can combine with two adjacent carbon atoms to form a ring. Usually, this occurs when the symbol is a double bond and n is 2. Examples of such rings include cycloalkene rings corresponding to the groups exemplified by "cycloalkenyl group", and non-aromatic heterocyclic rings corresponding to the groups having a carbon-carbon double bond among the groups exemplified by "non-aromatic heterocyclic group".

[0053] The ring may have one or more substituents. Examples of such substituents include hydrocarbon groups, halo groups, nitro groups, cyano groups, oxo groups, thioxo groups, carboxyl groups, sulfo groups, sulfamoyl groups, sulfinamoyl groups, sulfenamoyl groups, R r O-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R r OSO2- (in these formulas, R r has the same meaning as defined above). The number of such substituents can be selected from the range of 1 to the maximum number that can be substituted (e.g., 1, 2, 3, 4, 5).

[0054] Preferred examples of compound (1) are of formula (1A):

Chemical formula

Chem.

Chem.

[0055] In one embodiment of the compound (1A), preferably, R 11 , R 12 , and R 21 are independently a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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 R 22 is a hydrogen atom, more preferably, R 11 , R 12 , and R 21is, independently, a hydrogen atom, a halogen atom, an alkyl group which may be substituted with one or more halo groups, an alkoxy group which may be substituted with one or more halo groups, an alkoxyalkyl group which may be substituted with one or more halo groups, an alkylcarbonyl group which may be substituted with one or more halo groups, an alkylcarbonyloxy group which may be substituted with one or more halo groups, an alkoxycarbonyl group which may be substituted with one or more halo groups, 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 R 22 is a hydrogen atom.

[0056] In the above embodiment, preferably, R 11 and R 21 are, independently, a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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 R 12 and R 22 are hydrogen atoms, more preferably, R 11 and R 21is, independently, a hydrogen atom, a halogen atom, an alkyl group which may be substituted with one or more halo groups, an alkoxy group which may be substituted with one or more halo groups, an alkoxyalkyl group which may be substituted with one or more halo groups, an alkylcarbonyl group which may be substituted with one or more halo groups, an alkylcarbonyloxy group which may be substituted with one or more halo groups, an alkoxycarbonyl group which may be substituted with one or more halo groups, 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 R 12 and R 22 is a hydrogen atom.

[0057] In the above embodiment, Preferably, R 11 is a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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, R 21 is a hydrogen atom, 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 R 12 and R 22 are hydrogen atoms, More preferably, R 11is a hydrogen atom, a halogen atom, an alkyl group which may be substituted with one or more halo groups, an alkoxy group which may be substituted with one or more halo groups, an alkoxyalkyl group which may be substituted with one or more halo groups, an alkylcarbonyl group which may be substituted with one or more halo groups, an alkylcarbonyloxy group which may be substituted with one or more halo groups, an alkoxycarbonyl group which may be substituted with one or more halo groups, 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 R 21 is a hydrogen atom, 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 R 12 and R 22 is a hydrogen atom.

[0058] In the above embodiment, the substituent can be any group having a structure capable of substitution on the target. For example, it can be at least one selected from the group consisting of a halo group, a hydroxyl group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyl group, an arylcarbonyloxy group, an aryloxycarbonyl group, and an aryl group. The number of the substituents can be selected from within the range from 1 to the maximum number capable of substitution (e.g., 1, 2, 3).

[0059] In one embodiment of the compound (1A), R 11 and R 12 , or R 21 and R 22can form a ring together with one adjacent carbon atom. Examples of such rings include cycloalkane rings (e.g., C5-C7 cycloalkane rings such as cyclohexane rings) corresponding to the groups exemplified by the "cycloalkyl group", and non-aromatic heterocyclic rings corresponding to the groups exemplified by the "non-aromatic heterocyclic group". The ring may have one or more substituents. Examples of such substituents include hydrocarbon groups, halo groups, nitro groups, cyano groups, oxo groups, thioxo groups, carboxyl groups, sulfo groups, sulfamoyl groups, sulfinamoyl groups, sulfenamoyl groups, R r O-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R r OSO2- (in these formulas, R r has the same meaning as described above.). The number of such substituents can be within the range from 1 to the maximum number that can be substituted (e.g., 1, 2, 3, 4, 5).

[0060] In one embodiment of the compound (1A), R 11 and R 21 , R 11 and R 22 , R 12 and R 21 , or R 12 and R 22 can form a ring together with two adjacent carbon atoms. Examples of such rings include cycloalkene rings (e.g., C5-C7 cycloalkene rings such as cyclohexene rings) corresponding to the groups exemplified by the "cycloalkenyl group", and non-aromatic heterocyclic rings corresponding to the groups having a carbon-carbon double bond among the groups exemplified by the "non-aromatic heterocyclic group". The ring may have one or more substituents. Examples of such substituents include hydrocarbon groups, halo groups, nitro groups, cyano groups, oxo groups, thioxo groups, carboxyl groups, sulfo groups, sulfamoyl groups, sulfinamoyl groups, sulfenamoyl groups, R r O-, R r CO-, R r COO-, R r SO2-, R r OCO-, and R rOSO2- (in these formulas, R r is as defined above.) can be included. The number of such substituents can be within the range from 1 to the maximum number that can be substituted (e.g., 1, 2, 3, 4, 5).

[0061] Preferred examples of compound (1A) are formulas (1a) to (1c):

Chemical Formula

[0062] In one embodiment of compound (1a), preferably, R 1a is an alkyl group which may have one or more substituents, or an aralkyl group which may have one or more substituents.

[0063] In one embodiment of compound (1b), preferably, R 1b and R 2b are each independently an aryl group which may have one or more substituents.

[0064] In one embodiment of compound (1c), preferably, R 1c is a hydrogen atom, an alkyl group which may have one or more substituents, or an aryl group which may have one or more substituents, and R 2c is an alkyl group which may have one or more substituents

[0065] In one embodiment of compound (1B), preferably, R 13 and R 23 are each independently a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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, more preferably, R 13 and R 23 are each independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted with one or more halo groups, an alkoxy group which may be substituted with one or more halo groups, an alkoxyalkyl group which may be substituted with one or more halo groups, an alkylcarbonyl group which may be substituted with one or more halo groups, an alkylcarbonyloxy group which may be substituted with one or more halo groups, an alkoxycarbonyl group which may be substituted with one or more halo groups, 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.

[0066] In the above embodiments, the substituent can be any group having a structure capable of substitution on the target. For example, it can be at least one selected from the group consisting of a halo group, a hydroxyl group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyl group, an arylcarbonyloxy group, an aryloxycarbonyl group, and an aryl group. The number of the substituents can be selected from within the range of 1 to the maximum number capable of substitution (e.g., 1, 2, 3).

[0067] Fluorine source (A) Among the fluorine sources (A), hydrogen fluoride can be used as an aqueous solution (hydrofluoric acid). The aqueous solution can be, for example, an aqueous solution having a hydrogen fluoride concentration of 10 to 70% by mass.

[0068] Examples of the hydrogen fluoride salts among the fluorine sources (A) include hydrogen fluoride amine salts and hydrogen fluoride ammonium salts.

[0069] In the hydrogen fluoride amine salt, the amine can be a chain amine or a cyclic amine.

[0070] Examples of the chain amines include aliphatic primary amines, aliphatic secondary amines, and aliphatic tertiary amines. Examples of the aliphatic primary amines include C1-C6 alkylamines such as methylamine, ethylamine, propylamine, butylamine, pentylamine, and hexylamine. Examples of the aliphatic secondary amines include di-C1-C6 alkylamines such as dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, and dihexylamine. Examples of the aliphatic tertiary amines include tri-C1-C6 alkylamines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, and N,N,N’,N’-tetramethylethylenediamine.

[0071] Examples of cyclic amines include aliphatic cyclic amines and aromatic cyclic amines. Examples of aliphatic cyclic amines include piperidine, piperazine, pyrrolidine, morpholine, N-methylpiperazine, N-methylpyrrolidine, 5-diazabicyclo[4.3.0]non-5-ene, and 1,4-diazabicyclo[2.2.2]octane. Examples of aromatic cyclic amines include pyridine, pyrimidine, pyrazine, quinoline, and imidazole.

[0072] Examples of ammonium hydrogen fluoride salts are of formula (A1): NQ4·xHF (A1) (wherein each Q is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group, and x is an integer of 1 or more) and include compounds represented by.

[0073] In one embodiment of compound (A1), Q is preferably an alkyl group, more preferably a C1-C6 alkyl group. x is preferably 1 to 10.

[0074] Preferred examples of compound (A1) include ammonium hydrogen fluoride (NH4F·HF), hydrogen fluoride-tetramethylammonium fluoride, hydrogen fluoride-tetraethylammonium fluoride, hydrogen fluoride-tetrapropylammonium fluoride, and hydrogen fluoride-tetrabutylammonium fluoride.

[0075] Among the fluorine sources (A), examples of fluoride salts are of formula (A2): M 1 F m1 (A2) (wherein, M 1 is an alkali metal or an alkaline earth metal; and m1 is 1 or 2 depending on the valence of M 1 (A2)) and include compounds represented by. In one embodiment of compound (A2),

[0076] In one embodiment of compound (A2), Preferably, M 1 is Li, Na, K, Ca, or Cs, more preferably, M 1 is Na, K, or Ca, even more preferably, M 1 is K.

[0077] The fluoride salt can preferably be an alkali metal fluoride salt [a compound (A2) in which M 1 is an alkali metal and m1 is 1].

[0078] The fluorine source (A) can be used alone or in combination of two or more kinds.

[0079] The amount of the fluorine source (A) used is not particularly limited. The lower limit of the amount of the fluorine source (A) used can be, for example, 0.1 mol or more, preferably 0.2 mol or more, more preferably 0.3 mol or more, even more preferably 0.4 mol or more, and particularly preferably 0.5 mol or more per 1 mol of the compound (1). The upper limit of the amount of the fluorine source (A) used can be, for example, 1000 mol or less, preferably 500 mol or less, more preferably 300 mol or less, even more preferably 100 mol or less, even more preferably 50 mol or less, and particularly preferably 10 mol or less per 1 mol of the compound (1). The amount of the fluorine source (A) used can be, for example, in the range of 0.1 to 1000 mol, preferably in the range of 0.2 to 500 mol, more preferably in the range of 0.3 to 100 mol, even more preferably in the range of 0.4 to 50 mol, and particularly preferably in the range of 0.5 to 10 mol.

[0080] The fluorine source (A) in the residue after the reaction may be trapped and discarded, but it is preferable to recover and reuse it from the viewpoint of production cost. The trapping of the residue after the reaction may be performed, for example, by washing with water or alkaline water.

[0081] Halogen source (B) other than fluorine In one embodiment of the halogen source (B), preferably, R 3is an alkali metal, an alkaline earth metal, 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, a non-aromatic heterocyclic group which may have one or more substituents, or a heteroaryl group which may have one or more substituents.

[0082] Examples of the alkali metal include Li, Na, K, and Cs. Examples of the alkaline earth metal include Mg and Ca.

[0083] The substituent can be any group having a structure capable of substitution on the target, and can be, for example, a halo group. The number of the substituents can be selected from within the range of 1 to the maximum number capable of substitution (e.g., 1, 2, 3).

[0084] R 3 is more preferably R 3 is an alkali metal or an alkyl group which may have one or more substituents, even more preferably R 3 is an alkali metal or an alkyl group, even still more preferably R 3 is an alkali metal or a C1-C6 alkyl group, particularly preferably R 3 is an alkali metal or a C1-C4 alkyl group.

[0085] In one embodiment of the halogen source (B), preferably, X is a chlorine atom, a bromine atom, or an iodine atom, more preferably, X is a chlorine atom or a bromine atom, even more preferably, X is a chlorine atom.

[0086] The halogen source (B) can be, for example, a hydrate.

[0087] Preferred examples of the halogen source (B) are of formula (B1): R3a ClO (B1) (wherein R 3a is an alkali metal or a C1-C4 alkyl group) and includes the compounds represented thereby.

[0088] The halogen source (B) can be used alone or in combination of two or more.

[0089] The amount of the halogen source (B) used is not particularly limited. The lower limit of the amount of the halogen source (B) used can be, for example, 0.1 mol or more, preferably 0.2 mol or more, more preferably 0.3 mol or more, per 1 mol of the compound (1). The lower limit of the amount of the halogen source (B) used can be, for example, 10 mol or less, preferably 9 mol or less, more preferably 8 mol or less, per 1 mol of the compound (1). The amount of the halogen source (B) used can be, for example, in the range of 0.1 to 10 mol, preferably in the range of 0.2 to 9 mol, more preferably in the range of 0.3 to 8 mol, per 1 mol of the compound (1).

[0090] The residual halogen source (B) after the reaction may be trapped and discarded, but it is preferable to recover and reuse it from the viewpoint of production cost. The trapping of the residual after the reaction may be carried out, for example, by washing with water or alkaline water.

[0091] BF 3 , N-halosuccinimide The reaction in the above step can be carried out in the presence or absence of BF3 and / or N-halosuccinimide, but it is preferable to carry out the reaction in the absence of BF3 and N-halosuccinimide.

[0092] Each component may be charged into the reaction system of the above step at once, charged in several portions, or charged continuously.

[0093] Solvent The reaction of the above process can be carried out in the presence or absence of a solvent. The solvent can be either a nonpolar solvent or a polar solvent. The solvent can be an ester, a ketone, an aromatic hydrocarbon, an alcohol, an ether, an amine, a nitrogen-containing polar organic compound, a nitrile, a halogenated hydrocarbon, an aliphatic hydrocarbon, a fluorinated solvent, a carbonate, or other solvents, or a combination thereof.

[0094] Examples of the ester as the solvent include ethyl acetate, butyl acetate, amyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, and preferred examples thereof include ethyl acetate.

[0095] Examples of the ketone as the solvent include acetone, methyl ethyl ketone, diethyl ketone, hexanone, methyl isobutyl ketone, heptanone, diisobutyl ketone, acetonylacetone, methyl hexanone, and acetophenone, cyclohexanone, diacetone alcohol, and preferred examples thereof include acetone.

[0096] Examples of the aromatic hydrocarbon as the solvent include benzene, toluene, xylene, and ethylbenzene, and preferred examples thereof include benzene and toluene.

[0097] Examples of the alcohol as the solvent include methanol, ethanol, n-propanol, isopropanol, n-butanol, pentanol, hexanol, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, trimethylene glycol, and hexanetriol, and preferred examples thereof include methanol and ethanol.

[0098] Examples of the ether as the solvent include diethyl ether, dibutyl ether, tetrahydrofuran, tetrahydropyran, dioxane, dimethoxyethane, diethylene glycol diethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether (PGME; also known as 1-methoxy-2-propanol), propylene glycol monoethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol diethyl ether, and anisole, and preferred examples thereof include diethyl ether and tetrahydrofuran.

[0099] Examples of the amine as the solvent include monoethanolamine, diethanolamine, and triethanolamine.

[0100] Examples of the nitrogen-containing polar organic compound as the solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, 2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone, and preferred examples thereof include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone.

[0101] Examples of the nitrile as the solvent include acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, and adiponitrile, and a preferred example thereof includes acetonitrile.

[0102] Examples of the halogenated hydrocarbon as the solvent include dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tetrachloroethane, trichloroethane, chlorobenzene, dichlorobenzene, and chlorotoluene, and preferred examples thereof include dichloromethane and chloroform.

[0103] Examples of the aliphatic hydrocarbon as the solvent include hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, and mineral spirit, and preferred examples thereof include cyclohexane and heptane.

[0104] Examples of the fluorinated solvent include perfluorobenzene, trifluorotoluene, ditrifluorobenzene, and trifluoroethanol, and preferred examples thereof include perfluorobenzene and trifluoroethanol.

[0105] Examples of the carbonate as the solvent include tetralin dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, ethylene carbonate, and propylene carbonate, and preferred examples thereof include ethylene carbonate and propylene carbonate.

[0106] Examples of the other solvents include acetic acid, pyridine, dimethyl sulfoxide, sulfolane, and water.

[0107] The solvent can preferably be at least one selected from aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, esters, nitriles, and water, more preferably at least one selected from aliphatic hydrocarbons, halogenated hydrocarbons, ethers, and water, and still more preferably a halogenated hydrocarbon.

[0108] The solvent can be used alone or in combination of two or more.

[0109] The amount of the solvent used is, for example, Based on 1 part by mass of the compound (1), usually in the range of 0 to 200 parts by mass, preferably in the range of 0 to 100 parts by mass, and more preferably in the range of 0 to 50 parts by mass can be.

[0110] Temperature and time The temperature of the above process is usually within the range of -78 to 200 °C, preferably within the range of -10 to 100 °C, more preferably within the range of 0 to 100 °C, and even more preferably within the range of 10 to 40 °C can be.

[0111] The time of the above process is usually within the range of 0.1 to 72 hours preferably within the range of 0.5 to 48 hours, and more preferably within the range of 1 to 36 hours can be.

[0112] The production method of the present disclosure may further include a step of isolating or purifying compound (1). The isolation or purification of compound (1) can be carried out by methods such as filtration, extraction, dissolution, concentration, precipitation, dehydration, adsorption, or chromatography, or a combination thereof.

[0113] [Halogenating agent] The halogenating agent of the present disclosure includes a fluorine source (A) and a halogen source (B) other than fluorine. The fluorine source (A) and the halogen source (B) are as described in [Method for producing a halogen adduct of compound (1)].

[0114] The molar ratio of the fluorine source (A) to the halogen source (B) is not particularly limited. The lower limit of the content of the fluorine source (A) can be, for example, 1 mol or more, preferably 1.5 mol or more, and more preferably 2 mol or more per 1 mol of the halogen source (B). The upper limit of the content of the fluorine source (A) can be, for example, 1000 mol or less, preferably 500 mol or less, and more preferably 300 mol or less per 1 mol of the halogen source (B). The content of the fluorine source (A) can be, for example, within the range of 1 to 1000 mol, preferably within the range of 1.5 to 500 mol, and more preferably within the range of 2 to 300 mol per 1 mol of the halogen source (B).

[0115] The halogenating agent of the present disclosure may contain BF3 and / or N-halosuccinimide, but preferably does not contain BF3 and N-halosuccinimide.

[0116] The halogenating agent of the present disclosure can be suitably used to add fluorine and halogens other than fluorine to the double bond or triple bond of compound (1).

Examples

[0117] Hereinafter, an embodiment of the present disclosure will be described in more detail by way of examples, but the present disclosure is not limited thereto.

[0118] A solution of the substrate (1 mmol) shown in Table 1 in dichloromethane (6 mL) was cooled to 0 °C in an ice bath, and HF·pyridine (0.2 mL, 10 mmol HF) was added. Then, NaOCl·5H2O (298 mg, 4 mmol) was added all at once while stirring vigorously. The reaction solution was stirred at 0 °C for 2 hours. An aqueous solution of sodium thiosulfate (1.3 g) and water (20 mL) was added to the reaction solution, neutralized with NaHCO3, and then extracted with dichloromethane (20 mL×3). The extracted dichloromethane solution was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 19 The yield of the main product was determined by 19FNMR. The main product was separated by silica gel column chromatography.

[0119]

Table 1

[0120] A solution of the substrate (1 mmol) shown in Table 2 in dichloromethane (6 mL) was cooled to 0 °C in an ice bath, and HF·pyridine (0.2 mL, 10 mmol HF) was added. Then, tert-BuOCl (0.45 mL, 4 mmol) was added, and the reaction solution was stirred at 0 °C for 2 hours. An aqueous solution of sodium thiosulfate (1.3 g) and water (20 mL) was added to the reaction solution, neutralized with NaHCO3, and then extracted with dichloromethane (20 mL × 3). The extracted dichloromethane solution was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 19 The yield of the product was determined by 19F NMR. The main product was separated by silica gel column chromatography.

[0121]

Table 2

[0122] The above examples show an example using the compound (1) having a double bond as the substrate, but it is not limited thereto. The compound (1) having a triple bond basically has a strong tendency of having less steric hindrance and a higher reactivity than the compound (1) having a double bond. Therefore, from the results of the above examples, it can be said that the reaction proceeds similarly when the compound (1) having a triple bond is used as the substrate.

Claims

1. Formula (1): 【Chemical 1】 (In the formula,[[]] R １ and R ２ are, independently, a hydrogen atom,[[]] a halogen atom,[[]] an alkyl group which may have one or more substituents,[[]] an alkenyl group which may have one or more substituents,[[]] an alkynyl group which may have one or more substituents,[[]] a cycloalkyl group which may have one or more substituents,[[]] a cycloalkenyl group which may have one or more substituents,[[]] a cycloalkadienyl group which may have one or more substituents,[[]] an aryl group which may have one or more substituents,[[]] an aralkyl group which may have one or more substituents,[[]] a non-aromatic heterocyclic group which may have one or more substituents,[[]] a heteroaryl group which may have one or more substituents,[[]] a cyano group,[[]] an aldehyde group,[[]] a carboxyl group,[[]] R ｒ O−, R ｒ CO−、 R ｒ COO−、 R ｒ SO ２ -、 R ｒ OCO-, or R ｒ OSO ２ - (In these formulas, R ｒ is independently an alkyl group which may have one or more substituents,[[]] an alkenyl group which may have one or more substituents,[[]] an alkynyl group which may have one or more substituents,[[]] a cycloalkyl group which may have one or more substituents,[[]] a cycloalkenyl group which may have one or more substituents,[[]] a cycloalkadienyl group which may have one or more substituents,[[]] an aryl group which may have one or more substituents,[[]] an aralkyl group which may have one or more substituents,[[]] a non-aromatic heterocyclic group which may have one or more substituents, or[[]] a heteroaryl group which may have one or more substituents.) Or it may form a ring together with two adjacent carbon atoms,[[]] n is 1 or 2,[[]] symbol: 【Chemical 2】 is a double bond or a triple bond. However,[[]] when the symbol is a triple bond, n is 1,[[]] when the symbol is a double bond, n is 2,[[]] Two Rs １ may be identical to or different from each other, Two Rs ２ may be identical to or different from each other, or Two Rs １ or two Rs ２ may each together with adjacent carbon atoms form a ring.) A method for producing a halogen adduct of a compound represented by[[]] The compound represented by the formula (1) is (A) at least one fluorine source selected from the group consisting of hydrogen fluoride, hydrogen fluoride salts, and fluoride salts, and Formula (B): R ３ (OX) ｍ (In the formula, R ３ is an alkali metal or an alkaline earth metal, X is a halogen atom other than a fluorine atom, and m is an integer corresponding to the valence of R ３ ) A halogen source other than fluorine represented by reacting with to add fluorine and a halogen other than fluorine to the double bond or triple bond.

2. The production method according to claim 1, wherein the fluorine source (A) is at least one selected from the group consisting of hydrogen fluoride, hydrogen fluoride amine salts, and alkali metal fluoride salts.

3. The production method according to claim 1 or 2, wherein the amount of the fluorine source (A) used is in the range of 0.1 to 1000 moles per mole of the compound represented by the formula (1).

4. The production method according to any one of claims 1 to 3, wherein in the halogen source (B) other than fluorine, X is a chlorine atom.

5. The halogen source (B) other than fluorine is represented by the formula: R ３ａ ClO (wherein R ３ａ is an alkali metal), and the production method according to any one of claims 1 to 4.

6. The production method according to any one of claims 1 to 5, wherein the amount of the halogen source (B) other than fluorine used is in the range of 0.1 to 10 moles per 1 mole of the compound represented by the formula (1).

7. R １ and R ２ is independently a hydrogen atom, a halogen atom, an alkyl group which may have one or more substituents, an alkoxy group which may have one or more substituents, an alkylcarbonyl group which may have one or more substituents, an alkylcarbonyloxy group which may have one or more substituents, an alkoxycarbonyl 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, or R １ and R ２ together with two adjacent carbon atoms may form a ring, the production method according to any one of claims 1 to 6.

8. The production method according to claim 7, wherein the substituent is at least one selected from the group consisting of a halo group, a hydroxyl group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyl group, an arylcarbonyloxy group, an aryloxycarbonyl group, and an aryl group.

9. The compound represented by the formula (1) is any of the following formulas (1a) to (1c): 【Chemical Formula 3】 (In the formula, R １ａ is an alkyl 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 R １ｂ and R ２ｂ are independently an alkyl 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. R １ｃ is a hydrogen atom, an alkyl 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, R ２ｃ is an alkyl group which may have one or more substituents) The production method according to any one of claims 1 to 8, which is any of the compounds represented by.

10. The production method according to any one of claims 1 to 9, wherein the reaction is carried out in the presence of a solvent.

11. The production method according to claim 10, wherein the solvent is at least one selected from the group consisting of an aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated hydrocarbon, an ether, an ester, a nitrile, and water.

12. (A) At least one fluorine source selected from the group consisting of hydrogen fluoride, hydrogen fluoride salt, and fluoride salt, and Formula (B): R ３ (OX) ｍ (In the formula, R ３ is an alkali metal or an alkaline earth metal, X is a halogen atom other than a fluorine atom, and m is an integer corresponding to the valence of R ３ ) A halogen source other than fluorine represented by including The content of the fluorine source (A) is in the range of 1.5 to 500 moles per 1 mole of the halogen source (B). Halogenating agent.

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