Hydrochloric Acid → 1-(4-Bromo-2,5-difluorophenyl)ethan-1-one

HRID 1461375

Reaction equation

HRID 1461375 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[Br:9].[Cl-].[Al+3].[Cl-].[Cl-].[C:14](Cl)(=[O:16])[CH3:15].Cl>>[CH3:15][C:14]([C:6]1[C:5]([F:8])=[CH:4][C:3]([Br:9])=[C:2]([F:1])[CH:7]=1)=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 678622-Bromo-1,4-difluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 99916531-(4-Bromo-2,5-difluorophenyl)ethan-1-oneYield 76%

Conditions

Temperature
95 °C

Procedure

To a stirred mixture of 20 g 2,5-difluorobromobenzene and 35.2 g aluminum chloride under nitrogen at 60° C. was added dropwise 11.2 ml acetyl chloride. The reaction mixture was stirred at 95° C. for 90 min. and then poured over 250 g ice followed by 17 ml concentrated hydrochloric acid. The aqueous mixture was extracted with ether, and the extracts washed with sodium chloride solution and concentrated. The residue (23.6 g) was distilled in vacuo to give 18.4 g (76%) 4-bromo-2,5-difluoroacetophenone, b.p. 65° C. (0.1 mm).

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. washthe extracts washed with sodium chloride solution
  3. concentrationconcentrated
  4. distillationThe residue (23.6 g) was distilled in vacuo

Sources & evidence

ORD record
ord-5c450a7c40c84a15ae114145587651b6
Source dataset
uspto-grants-1991_12
Patent number
US05075319

Linked notes

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