Potassium Carbonate → trans 2-Bromo-6-chlorobenzyl 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylate

HRID 128245Notes

Reaction equation

HRID 128245 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C:6]([CH3:8])([CH3:7])[C@H:5]1[C:9]([OH:11])=[O:10].[Br:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:15]=1[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C:6]([CH3:8])([CH3:7])[C@H:5]1[C:9]([O:11][CH2:16][C:15]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:14]=1[Br:13])=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 41539Trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acidHCID 27568722-Bromo-6-chlorobenzyl bromide

Product 1

HCID 131712138trans 2-Bromo-6-chlorobenzyl 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1 cis/trans 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropane carboxylic acid (2.3 g), 2-bromo-6-chlorobenzylbromide (2.85 g) and potassium carbonate (1.6 g) were stirred together in acetone (30 ml) under reflux for 6 hours. The reaction mixture was cooled, diluted with water, and extracted three times with 50 ml portions of diethyl ether. The combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times), dried over magnesium sulphate and evaporated to give the orange title product (4. g, 98%) m.p. 61°-67° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted three times with 50 ml portions of diethyl ether
  4. washThe combined ether extracts were washed with water and with aqueous sodium bicarbonate solution (three times)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-86a8a7b9788b4e6e9447e9f7d06881be
Source dataset
uspto-grants-1981_03
Patent number
US04259349

Reaction notes

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