Method of manufacturing fluorine-containing compound

Patent metadata

Field	Value
Publication number	US-12577199-B2
Application number	US-202217698102-A
Country	US
Kind code	B2
Filing date	Mar 18, 2022
Priority date	Sep 20, 2019
Publication date	Mar 17, 2026
Grant date	Mar 17, 2026

Abstract

The present invention is directed to providing a method of manufacturing a fluorine-containing compound according to which a fluorine-containing compound is manufactured under a relatively moderate reaction condition by use of a readily available compound. A method of manufacturing a fluorine-containing compound includes reacting a compound having a partial structure expressed by a formula (a) below with a Grignard reagent in the presence of a transition metal compound,

—CF 2 —CH 2 -L  (a)

wherein L is a sulfonate group.

First claim

What is claimed is:

1 . A method of manufacturing a fluorine-containing compound, comprising:
reacting a compound of Formula (A1) or Formula (A2), with a Grignard reagent of Formula (B), in the presence of a transition metal compound, and obtaining a fluorine-containing compound of a formula G 1 -CF 2 —CH 2 —R if the starting material is of Formula (A1), or obtaining a fluorine-containing compound of a formula R—CH 2 (—CF 2 -G 2 ) n -CF 2 —CH 2 —R if the starting material is of Formula (A2),
G 1 -CF 2 —CH 2 -L  Formula (A1)

L-CH 2 (—CF 2 -G 2 ) n -CF 2 —CH 2 -L  Formula (A2)

R—MgX  Formula (B)

wherein
G 1 is a monovalent group having a (poly)oxyfluoroalkylene chain, a hydrogen atom, an alkyl group, or a fluoroalkyl group,
G 2 is a divalent group having a (poly)oxyfluoroalkylene chain, a single bond, an alkylene group, or a fluoroalkylene group,
L is a sulfonate group, and a plurality of L's in the formula (A2) may be identical to or different from each other,
R is a hydrocarbon group optionally including a substituent and/or a heteroatom within a carbon chain,
X is a halogen atom, and
n is 0 or 1.

2 . The method of manufacturing a fluorine-containing compound according to claim 1 , wherein G 1 is a monovalent group having a (poly)oxyfluoroalkylene chain or a perfluoroalkyl group.

3 . The method of manufacturing a fluorine-containing compound according to claim 1 , wherein,
n is 1, and G 2 is a divalent group having a (poly)oxyfluoroalkylene chain, a single bond, or a perfluoroalkylene group.

4 . The method of manufacturing a fluorine-containing compound according to claim 1 , wherein the Grignard reagent is of Formula (B1),
R 1 —CH 2 —MgX  Formula (B1)
wherein R 1 is a hydrogen atom or a hydrocarbon group optionally including a substituent and/or a heteroatom within a carbon chain, and X is a halogen atom.

5 . The method of manufacturing a fluorine-containing compound according to claim 1 , wherein L is a triflate group.

6 . The method of manufacturing a fluorine-containing compound according to claim 1 , wherein the transition metal compound comprises copper.

Assignees

• Agc Inc

Inventors

• Takashita Ryuta

Classifications

• C07C17/2632 Primary

  involving an organo-magnesium compound, e.g. Grignard synthesis · CPC title

• C07B49/00

  Grignard reactions · CPC title

• C07C43/17

  containing halogen · CPC title

• C07C19/14

  and bromine · CPC title

• C07C41/30

  by increasing the number of carbon atoms, e.g. by oligomerisation · CPC title