Thionyl Chloride → cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

HRID 1414055Notes

Reaction equation

HRID 1414055 reaction equation
[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:10])([F:9])[F:8])[C@@H:3]1[C:12](O)=[O:13].S(Cl)([Cl:18])=O>>[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:10])([F:9])[F:8])[C@@H:3]1[C:12]([Cl:18])=[O:13]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54318404cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Procedure

10 g of cis-2,2-dimethyl-3-(2'-chloro-3',3',3'-trifluoropropenyl)-cyclopropanecarboxylic acid were dissolved in 50 ml of thionyl chloride and the solution was heated to the boil for one hour. After distilling off the excess thionyl chloride, the residue was distilled under a high vacuum. Cis-2,2-dimethyl-3-(2'-chloro-3',3',3'-trifluoropropenyl)-cyclopropanecarboxylic acid chloride of boiling point 52°-54° C./0.9 mm Hg and nD20 : 1.4520 was obtained.

Workup

  1. temperaturethe solution was heated to the boil for one hour
  2. distillationAfter distilling off the excess thionyl chloride
  3. distillationthe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-bbf63f459f29413baa9835153ac66e37
Source dataset
uspto-grants-1981_02
Patent number
US04252820

Reaction notes

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