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

HRID 1681184Notes

Reaction equation

HRID 1681184 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-3de26d3486fc44f4a2f4ede52cebe853
Source dataset
uspto-grants-1992_12
Patent number
US05169853

Reaction notes

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