Iodine → 2-Chloro-3,5-difluoro-4-methylbenzoyl chloride

HRID 34589Notes

Reaction equation

HRID 34589 reaction equation
[Cl:1]Cl.[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([F:14])[C:12]=1[CH3:13])[C:7]([Cl:9])=[O:8].II>>[F:3][C:4]1[CH:5]=[C:6]([C:10]([Cl:1])=[C:11]([F:14])[C:12]=1[CH3:13])[C:7]([Cl:9])=[O:8]

Participants

4

Reactant 3

HCID 807IodineHCID 24526ChlorineHCID 136574553,5-Difluoro-4-methylbenzoyl chloride

Product 1

HCID 136574602-Chloro-3,5-difluoro-4-methylbenzoyl chlorideYield 53.2%

Procedure

30 g of chlorine are passed into 70 g of 3,5-difluoro-4-methyl-benzoyl chloride and a spatula-tip of FeS and I2 at 40°-45°, with slight cooling. The mixture is then flushed with nitrogen, the residue is coarsely distilled and the distillate is fractionated. 44 g of 3,5-difluoro-4-methyl-6-chlorobenzoyl chloride of boiling point: 109°/16 mbar, nD20 : 1.5342 are obtained. 3,5-Difluoro-2,6-dichloro-4-methyl-benzoyl chloride of boiling point b.p: 109°/13 mbar, nD20 : 1.5274 are obtained from the last runnings.

Workup

  1. customat 40°-45°
  2. customThe mixture is then flushed with nitrogen
  3. distillationthe residue is coarsely distilled

Sources & evidence

ORD record
ord-871f95620d28494d83205aa04269860f
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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