Thionyl Chloride → trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chloride

HRID 2052374Notes

Reaction equation

HRID 2052374 reaction equation
[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].S(Cl)([Cl:18])=O>>[Cl:18][C:7]([C@H:6]1[C@H:4]([CH:3]=[C:2]([Cl:1])[C:12]([F:15])([F:14])[F:13])[C:5]1([CH3:11])[CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86736787trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86736786trans-3-[2-Chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarbonyl chloride

Procedure

A mixture of (+)-cis/trans-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid (0.4 g) and thionyl chloride (5.0 ml) was heated at the reflux temperature for a period of 2 hours, after which the excess thionyl chloride was removed by distillation under reduced pressure, leaving (+)-cis/trans-1-chlorocarbonyl-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane.

Workup

  1. temperaturewas heated at the reflux temperature for a period of 2 hours
  2. customafter which the excess thionyl chloride was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-cd11ba3892f740c9bc241a27b205c977
Source dataset
uspto-grants-1980_01
Patent number
US04183948

Reaction notes

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