Method of producing compound having butadiene skeleton containing hydrogen and fluorine and/or chlorine

Patent metadata

Field	Value
Publication number	US-11046629-B2
Application number	US-201916959317-A
Country	US
Kind code	B2
Filing date	Feb 1, 2019
Priority date	Feb 2, 2018
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A1A2C═CA3-CA4=CA5A6 [A1, A2, A5, and A6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A3 and A4 are each independently hydrogen, fluorine, or chlorine; at least one of A1 to A6 is hydrogen; at least one of A1 to A6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A7A8C═CA9X [A7 and A8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

First claim

The invention claimed is:

1. A method of producing a halogenated diene represented by formula (1):

wherein: A 1 , A 2 , A 5 , and A 6 are each independently hydrogen, fluorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group;
A 3 and A 4 are each independently hydrogen or fluorine; and
at least one of A 1 to A 6 is hydrogen, and at least one of A 1 to A 6 is fluorine,
the method comprising a step of subjecting the same or different halogenated olefin(s) represented by formula (2) to a coupling reaction in the presence of a zero-valent metal and a metal salt:

wherein: A 7 and A 8 are each independently hydrogen, fluorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group;
A 9 is each independently hydrogen or fluorine; and
X is bromine or iodine,
wherein the zero-valent metal and the metal of the metal salt are copper.

2. The method according to claim 1 , comprising the step of subjecting the same halogenated olefin to a coupling reaction.

3. The method according to claim 1 , comprising the step of subjecting the different halogenated olefins to a coupling reaction.

4. The method according to claim 1 , wherein at least one of the halogenated olefin(s) represented by formula (2) is 1,1-difluoro-2-iodoethylene.

5. The method according to claim 1 , wherein the step of subjecting to a coupling reaction is performed in a solvent or in the absence of solvent.

6. The method according to claim 5 , wherein the solvent is present as one or more amide solvents.

7. The method according to claim 1 , wherein a reaction temperature in the step of subjecting to a coupling reaction is within a range of 20° C. to 200° C.

Assignees

• Kanto Denka Kogyo Kk

Inventors

• Kashikura Wataru
• Iketani Yoshihiko
• Kimura Ryo
• Shibusawa Yukinobu

Classifications

• C07C17/269 Primary

  of only halogenated hydrocarbons · CPC title

• C07B61/00

  Other general methods · CPC title

• C07C17/26

  by reactions involving an increase in the number of carbon atoms in the skeleton · CPC title

• C07C17/278

  of only halogenated hydrocarbons · CPC title

• C07C17/263

  by condensation reactions · CPC title