Thionyl Chloride → HCID 54563404, compound

HRID 1277987Notes

Reaction equation

HRID 1277987 reaction equation
[CH3:1][C:2]1([CH3:18])[CH:4]([CH:5]=[C:6]([Br:14])[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[CH:3]1[C:15](O)=[O:16].S(Cl)([Cl:21])=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:18])[CH:4]([CH:5]=[C:6]([Br:14])[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[CH:3]1[C:15]([Cl:21])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54013597HCID 54013597, compound

Product 1

HCID 54563404HCID 54563404, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

59 g (0.2 mol) of 2,2-dimethyl-3-(2-bromo-2-(4-chloro-phenyl)-vinyl)-cyclopropanecarboxylic acid were dissolved in 500 ml of carbon tetrachloride, and 119 g of thionyl chloride were slowly added dropwise at 25° C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. When the reaction period had ended, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. The oil which remained was distilled. 33.7 g (53.8% of theory) of 2,2-dimethyl-3-(2-bromo-2-(4-chloro-phenyl)-vinyl)-cyclopropanecarboxylic acid chloride were obtained as a colorless liquid with a boiling point of 165°-166° C. under 8 mm Hg.

Workup

  1. temperatureThe mixture was then heated to the reflux temperature for 4 hours
  2. customWhen the reaction period
  3. distillationexcess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum
  4. distillationThe oil which remained was distilled

Sources & evidence

ORD record
ord-536f28cf0cd548f6b103375981f6c48d
Source dataset
uspto-grants-1981_07
Patent number
US04279920

Reaction notes

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