Method for producing difluoromethylene compound

Patent metadata

Field	Value
Publication number	US-11377407-B2
Application number	US-201917048760-A
Country	US
Kind code	B2
Filing date	Apr 25, 2019
Priority date	Apr 25, 2018
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

The problem to be solved by the present invention is to provide a novel method for producing a difluoromethylene compound, in particular, a simple method for producing a difluoromethylene compound. This problem is solved by a method for producing a difluoromethylene compound (I) containing at least one —CF2— moiety, the method comprising step A of allowing IF5 and a disulfide compound (III) of the formula: RA—S—S—RA (wherein RA, in each occurrence, independently represents aryl optionally having at least one substituent or alkyl optionally having at least one substituent) to act on a carbonyl compound (II) containing at least one —C(O)— moiety.

First claim

The invention claimed is:

1. A method for producing a difluoromethylene compound (I) containing at least one —CF 2 — moiety, the method comprising step A of reacting IF 5 and
a disulfide compound (III) of the formula: R A —S—S—R A , wherein R A , in each occurrence, independently represents aryl optionally having at least one substituent or alkyl optionally having at least one substituent, with
a carbonyl compound (II) containing at least one —C(O)— moiety.

2. The production method according to claim 1 ,
wherein
the difluoromethylene compound (I) is a difluoromethylene compound represented by formula (1):
R 11 —C 2 —R 12   (1),

wherein R 11 and R 12 are identical or different, and each represents
(a) an organic group optionally containing at least one —CF 2 — moiety or
(b) fluorine, and
the carbonyl compound (II) is a carbonyl compound represented by formula (2):
R 21 —C(O)—R 22   (2),

wherein R 21 and R 22 are identical or different, and each represents
(a) hydrogen,
(b) hydroxyl, or
(c) an organic group optionally containing at least one —CO— moiety, or R 21 and R 22 , taken together with the adjacent —C(O)— moiety, may form a ring, with the proviso that
neither R 11 nor R 12 , and neither R 21 nor R 22 , is an organic group bonded via —O—.

3. The production method according to claim 1 ,
wherein
the difluoromethylene compound (I) is a difluoromethylene compound represented by formula (1):
R 11 —CF 2 —R 12   (1),

wherein
R 11 represents R 21 or fluorine,
R 12 represents R 22 or fluorine,
R 21 and R 22 are identical or different, and each represents
(a) hydrogen,
(b) hydroxyl, or
(c) an organic group, or
R 21 and R 22 , taken together with the adjacent —CF 2 — moiety, may form a ring,
with the proviso that
(i) neither R 11 nor R 12 is hydroxyl, and
(ii) neither R 11 nor R 12 , and neither R 21 nor R 22 , is an organic group bonded via —O—, and the carbonyl compound (II) is a carbonyl compound represented by formula (2):
R 21 —C(O)—R 22   (2),

wherein
the symbols in the formula are as defined above.

4. The production method according to claim 1 , further comprising reacting at least one member selected from the group consisting of acids, salts, and additives in addition to IF 5 .

5. The production method according to claim 1 , further comprising reacting an acid and a base in addition to IF 5 .

6. The production method according to claim 4 , wherein the acid is hydrogen fluoride.

7. The production method according to claim 5 , wherein the base is a 5-membered monocyclic nitrogen-containing aromatic heterocyclic compound optionally substituted with one or more alkyl groups.

8. The production method according to claim 1 , wherein R A , in each occurrence, independently represents aryl optionally having at least one substituent.

9. The production method according to claim 5 , wherein the acid is hydrogen fluoride.

10. The production method according to claim 9 , wherein the base is a 5-membered monocyclic nitrogen-containing aromatic heterocyclic compound optionally substituted with one or more alkyl groups.

Assignees

• Daikin Ind Ltd

Inventors

• Ohtsuka Tatsuya
• Kuroki Yoshichika
• Shirai Atsushi
• Hosokawa Moe
• Kishikawa Yosuke

Classifications

• C07C17/361 Primary

  by reactions involving a decrease in the number of carbon atoms · CPC title

• C07C17/18

  of oxygen atoms of carbonyl groups · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C17/32 Primary

  by introduction of halogenated alkyl groups into ring compounds · CPC title

• C07C22/08

  containing fluorine · CPC title