Thionyl Chloride → 2-Chloro-4,5-difluorobenzoyl chloride

HRID 249291Notes

Reaction equation

HRID 249291 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 7371712-Chloro-4,5-difluorobenzoic acid

Product 1

HCID 101982172-Chloro-4,5-difluorobenzoyl chlorideYield 90%

Procedure

2-Chloro-4,5-difluorobenzoic acid (19.2 g, 0.1 mol) was mixed with thionyl chloride (50 ml) and heated to reflux for 3 hours. The reaction mixture was evaporated to dryness, and the residue dissolved in methylene chloride. Solvent was removed in vacuo, and the procedure repeated once with methylene chloride and once with benzene. The material (19 g, 0.09 mol, 90% yield) was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionthe residue dissolved in methylene chloride
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-7d0537f4877244f3a8ed1ae02e654a92
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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