Fluoroacetyl chloride → Ethanone, 1-(2,4-difluorophenyl)-2-fluoro- (9CI)

HRID 1087769Notes

Reaction equation

HRID 1087769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:13][CH2:14][C:15](Cl)=[O:16]>C(Cl)Cl>[F:13][CH2:14][C:15]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[F:8])=[O:16]

Participants

5

Reactant 3

HCID 9663Fluoroacetyl chlorideHCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22163867Ethanone, 1-(2,4-difluorophenyl)-2-fluoro- (9CI)Yield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,3-Difluorobenzene (2.02 g; 17.7 mM) and anhydrous aluminium chloride (2.60 g; 19.47 mM) were stirred together under dry nitrogen at room temperature. A solution of fluoroacetyl chloride (1,71 g; 17.7 mM) in anhydrous methylene chloride (2 ml) was added over 30 minutes. The mixture was then warmed at about 50° for 3 hours. On cooling methylene chloride (40 ml) was added and the mixture was poured onto ice. The methylene chloride layer was separated, dried over magnesium sulphate and evaporated to give a white solid. This material was chromatographed on a column of silica eluting with a mixture of hexane/methylene chloride (65:35 by volume). The product-containing fractions were collected. The title compound crystallised on evaporation of these fractions and was dried in a vacuum desiccator to a colourless crystalline solid (1.12 g; 36% yield), melting point 57°-8°.

Workup

  1. temperatureThe mixture was then warmed at about 50° for 3 hours
  2. additionwas added
  3. additionthe mixture was poured onto ice
  4. customThe methylene chloride layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customto give a white solid
  8. customThis material was chromatographed on a column of silica eluting with a mixture of hexane/methylene chloride (65:35 by volume)
  9. customThe product-containing fractions were collected
  10. customThe title compound crystallised on evaporation of these fractions
  11. customwas dried in a vacuum desiccator to a colourless crystalline solid (1.12 g; 36% yield), melting point 57°-8°

Sources & evidence

ORD record
ord-7ca23e2bb9bb430c8b66d606524e0378
Source dataset
uspto-grants-1990_10
Patent number
US04960782

Reaction notes

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