Thionyl Chloride → 2,5-Difluoro-4-Methylbenzoyl chloride

HRID 34592Notes

Reaction equation

HRID 34592 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>>[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 136574512,5-Difluoro-4-methylbenzoic acid

Product 1

HCID 136574572,5-Difluoro-4-Methylbenzoyl chloride

Procedure

250 ml of thionyl chloride are taken and 120 g of 2,5-difluoro-4-methyl-benzoic acid are introduced in portions at room temperature, with brisk evolution of gas. When the evolution of gas has subsided, the mixture is heated slowly to the reflux temperature and stirred until the evolution of gas has ended. The excess thionyl chloride is distilled off, the reaction product is coarsely distilled over and the distillate is fractionated on a small column. Yield: 97 g (72.9% of theory) of 2,5-difluoro-4-methylbenzoyl chloride of boiling point b.p.: 103°/20 mbar, nD20 : 1.5232.

Workup

  1. temperaturethe mixture is heated slowly to the reflux temperature
  2. distillationThe excess thionyl chloride is distilled off
  3. distillationthe reaction product is coarsely distilled over and the distillate

Sources & evidence

ORD record
ord-8f63d8c795b44489840f46bc733e1d03
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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