Chloroacetyl chloride → 2-Chloro-1-(2,4-difluorophenyl)ethanone

HRID 728336Notes

Reaction equation

HRID 728336 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][C:9]=1[F:13])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanoneYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (113 g, 1.0 mole) was added dropwise to a stirred mixture of 1,3-difluorobenzene (114 g, 1.0 mole) and anhydrous aluminum chloride (146.6 g, 1.1 mole) at room temperature (20° C.). The mixture was stirred for a further five hours at 50°-55° C. Methylene chloride (48.5 ml) was added slowly as the mixture was allowed to cool to room temperature. The methylene chloride layer was separated, washed with water (2×320 ml) and the solvent removed by distillation at reduced pressure leaving a pale yellow solid (180 g).

Workup

  1. customThe methylene chloride layer was separated
  2. washwashed with water (2×320 ml)
  3. customthe solvent removed by distillation at reduced pressure

Sources & evidence

ORD record
ord-c6fdcfea530b411d9dfdce2a89b47c47
Source dataset
uspto-grants-1991_09
Patent number
US05047548

Reaction notes

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