Acetyl chloride → 2'-Chloro-4',5'-difluoroacetophenone

HRID 974658Notes

Reaction equation

HRID 974658 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:2][C:1]([C:11]1[C:6]([Cl:5])=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=1)=[O:3]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 1365194-Chloro-1,2-difluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27364892'-Chloro-4',5'-difluoroacetophenoneYield 82%

Conditions

Temperature
120 °C

Procedure

23.6 g (0.3 mol) of acetyl chloride was added to a mixture comprising 29.7 g (0.2 mol) of 1-chloro-3,4-difluorobenzene and 40.0 g (0.3 mol) of aluminum chloride at a temperature of from 20° to 40° C. Then, the mixture was stirred at 120° C. for two hours. While still being hot, the mixture was poured on 250 g of ice, and the separated oil was extracted with ethylene chloride. The extract was neutralized and washed with water, and the solvent was distilled off under reduced pressure to obtain 31.2 g (yield: 82%) of 2-chloro-4,5-difluoroacetophenone. This compound was analyzed, and the analytical values were as follows.

Workup

  1. extractionthe separated oil was extracted with ethylene chloride
  2. washwashed with water
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-659cd691d1974f5183cd1cf7e269c820
Source dataset
uspto-grants-1991_11
Patent number
US05068449

Reaction notes

Loading…