Method for producing alpha-halogenoacetophenon compound, and alpha-bromoacetophenon compound

Patent metadata

Field	Value
Publication number	US-2016200654-A1
Application number	US-201615075744-A
Country	US
Kind code	A1
Filing date	Mar 21, 2016
Priority date	Sep 30, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A method for producing an α-halogenoacetophenon compound includes reacting a specific α-halogenocarboxylic halide compound and a specific phenyl compound in the presence of a Lewis acid in a solvent, in which the α-halogenoacetophenon compound and the phenyl compound are reacted with each other in a molar ratio of the Lewis acid to the phenyl compound represented below.
2≦Lewis acid/phenyl compound≦6

First claim

What is claimed is:

1 . A method for producing an α-halogenoacetophenon compound represented by Formula (3) below, comprising:
reacting an α-halogenocarboxylic halide compound represented by Formula (1) below and a phenyl compound represented by Formula (2) in the presence of a Lewis acid in a solvent,
wherein the α-halogenocarboxylic halide compound and the phenyl compound are reacted with each other in a molar ratio of the Lewis acid to the phenyl compound represented below,
2≦Lewis acid/phenyl compound≦6

in Formula (1), each of R 1 and R 2 independently represents an alkyl group, and each of X 1 and X 2 independently represents a halogen atom,

in Formula (2), each of R 3 to R 6 independently represents a hydrogen atom or a substituent, R 7 represents a hydrogen atom, an alkyl group, an acyl group, or a trialkylsilyl group, each of Y 1 and Y 2 independently represents an oxygen atom or a sulfur atom, and n represents an integer of 1 to 3, and

in Formula (3), R 1 , R 2 , and X 2 respectively have the same meanings as R 1 , R 2 , and X 2 in Formula (1), and R 3 to R 7 , Y 2 , and n respectively have the same meanings as R 3 to R 7 , Y 1 , Y 2 , and n in Formula (2).

2 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein, in Formula (1), X 1 represents a bromine atom.

3 . The method for producing an α-halogenoacetophenon compound according to claim 2 ,
wherein, in Formula (1), R 1 and R 2 are methyl.

4 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein aluminium (III) chloride is used as the Lewis acid.

5 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein R 7 in Formulae (2) and (3) is an alkylcarbonyl group or an arylcarbonyl group.

6 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein n in Formulae (2) and (3) is 2.

7 . The method for producing an α-halogenoacetophenon compound according to claim 2 ,
wherein n in General Formulae (2) and (3) is 2.

8 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein at least one selected from dichloromethane, chlorobenzene, sulfolane, ethyl acetate, acetonitrile, 1,3,5-trimethylbenzene, methyl ethyl ketone, and o-dichlorobenzene is used as the solvent.

9 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein, at least one selected from dichloromethane, chlorobenzene, and o-dichlorobenzene is used as the solvent.

10 . The method for producing an α-halogenoacetophenon compound according to claim 2 ,
wherein, at least one selected from dichloromethane, chlorobenzene, and o-dichlorobenzene is used as the solvent.

11 . The method for producing an α-halogenoacetophenon compound according to claim 6 ,
wherein, at least one selected from dichloromethane, chlorobenzene, and o-dichlorobenzene is used as the solvent.

12 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein o-dichlorobenzene is used as the solvent.

13 . The method for producing an α-halogenoacetophenon compound according to claim 2 ,
wherein o-dichlorobenzene is used as the solvent.

14 . The method for producing an α-halogenoacetophenon compound according to claim 6 ,
wherein o-dichlorobenzene is used as the solvent.

15 . The method for producing an α-halogenoacetophenon compound according to claim 12 ,
wherein the α-halogenocarboxylic halide compound and the phenyl compound are reacted with each other in a molar ratio of the o-dichlorobenzene to the phenyl compound represented below.
5≦o-dichlorobenzene/phenyl compound≦20

16 . The method for producing an α-halogenoacetophenon compound according to claim 13 ,
wherein the α-halogenocarboxylic halide compound and the phenyl compound are reacted with each other in a molar ratio of the o-dichlorobenzene to the phenyl compound represented below.
5≦o-dichlorobenzene/phenyl compound≦20

17 . The method for producing an α-halogenoacetophenon compound according to claim 12 ,
wherein aluminium (III) chloride as the Lewis acid and the α-halogenocarboxylic halide compound are mixed with each other, in the o-dichlorobenzene, and
the phenyl compound is subsequently mixed.

18 . The method for producing an α-halogenoacetophenon compound according to claim 1 ,
wherein the α-halogenocarboxylic halide compound and the phenyl compound are reacted under a temperature condition of 30° C. or lower.

19 . An α-bromoacetophenon compound represented by Formula (6) below,

wherein, in Formula (6), each of R 1 and R 2 independently represents an alkyl group, and R 7 represents a hydrogen atom, an alkyl group, an acyl group, or a trialkylsilyl group.

20 . The α-bromoacetophenon compound according to claim 19 ,
wherein, in Formula (6), R 1 and R 2 are methyl, and
R 7 is a hydrogen atom or acetyl.

Assignees

• Fujifilm Corp

Inventors

• Yofu Katsuyuki
• AMAO Akihito
• Shimono Katsuhiro

Classifications

• C07C49/84

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C45/46 Primary

  Friedel-Crafts reactions · CPC title

• C07C67/29

  by introduction of oxygen-containing functional groups · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title