# US 10,479,681 B2 · Fluorinating agent

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- Number: US 10,479,681 B2
- Document ID: US10479681B2
- Status: Granted
- Kind: B2
- Application number: 16/261,737
- Filed: 2019-01-30
- Published: 2019-05-23
- Granted: 2019-11-19
- Earliest claimed: 2013-10-02
- Assignees: Daikin Industries, Ltd.; National University Corporation Hokkaido University
- Applicants: Daikin Industries, Ltd.; National University Corporation Hokkaido University
- Inventors: Shoji Hara; Yosuke Kishikawa; Atsushi Shirai; Takashi Namikawa; Sumi Ishihara
- Web page: https://patentgrep.com/patent/US10479681B2

## CPC

- C01B 7/24: Inter-halogen compounds
- C01D 3/02: Fluorides
- C01D 13/00: Compounds of sodium or potassium not provided for elsewhere
- C07C 17/354: by hydrogenation
- C07C 17/361: by reactions involving a decrease in the number of carbon atoms
- C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C07C 45/63: by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C07C 45/673: {by change of size of the carbon skeleton}
- C07C 67/307: by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C07C 67/333: by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32)
- C07C 209/74: by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
- C07C 231/12: by reactions not involving the formation of carboxamide groups
- C07C 319/20: by reactions not involving the formation of sulfide groups
- C07D 209/10: with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D 309/10: Oxygen atoms
- C07D 493/04: Ortho-condensed systems
- C07C 2603/86: containing four rings
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C01D: COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM (metal hydrides {monoborane, diborane or addition complexes thereof} C01B6/00; salts of oxyacids of halogens C01B11/00; peroxides, salts of peroxyacids C01B15/00; sulfides C01B17/22; thiosulfates, dithionites, polythionates C01B17/64; compounds containing selenium or tellurium C01B19/00; binary compounds of nitrogen with metals C01B21/06; azides C01B21/08; {compounds other than ammonia and cyanogen, containing nitrogen and other non-metals C01B21/082}; metal amides C01B21/092; nitrites C01B21/50; phosphides C01B21/50; {compounds of noble gases C01B23/0005}; phosphides C01B25/08; salts of oxyacids of phosphorus C01B25/16; carbides C01B32/90; compounds containing silicon C01B33/00; compounds containing boron C01B35/00; cyanides C01C3/08; salts of cyanic acid C01C3/14; salts of cyanamide C01C3/16; thiocyanates C01C3/20)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

An object of the present invention is to provide a novel substance that has a high reactivity as a fluorinating agent, is effectively used in various fluorination reactions, and is safely handled even in air. As the solution for achieving this object, the present invention provides a complex obtained by reacting bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals in a nonpolar solvent. This complex serves as a fluorinating agent that provides excellent fluorination performance and that is stable in air.

## Claims

### Claim 1

A method for fluorinating a compound, the method comprising:
bringing the compound into contact with a complex consisting of bromine trifluoride and at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the complex exhibits an exothermic decomposition onset temperature in nitrogen of 40° C. or higher.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the complex is a reaction product obtained by mixing bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals, in a nonpolar solvent.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the reaction product is obtained by reacting 0.5 mol or more of the metal halide, per mol of bromine trifluoride.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the metal halide is at least one member selected from the group consisting of a halogenated metal represented by the formula: MX, wherein M is M1 or (M2)1/2), M1 is an alkali metal, and M2 is an alkaline earth metal, and X is a halogen atom; and a halogenated metal represented by the formula: MHX2, wherein M and X are as defined above.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the metal halide is at least one potassium halide selected from the group consisting of halogenated potassium and halogenated hydrogen potassium.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the metal halide is at least one potassium fluoride selected from the group consisting of fluorinated potassium and fluorinated hydrogen potassium.