Acetone → 2-chloro-4-fluorobenzyl(+/-)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate

HRID 1285387Notes

Reaction equation

HRID 1285387 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]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:24]=1[CH2:25]Br.CC(C)=O>C(OCC)C>[Cl:1]/[C:2](/[C:12]([F:13])([F:14])[F:15])=[CH:3]\[C@@H:4]1[C@H:6]([C:7]([O:9][CH2:25][C:24]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:23]=2[Cl:22])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 11184106(1S-cis)-Cyhalothric acid

Product 1

HCID 1317145092-chloro-4-fluorobenzyl(+/-)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylateYield 69.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (±)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid (1.20 g), anhydrous potassium carbonate (2.0 g), 2-chloro-4-fluorobenzyl bromide (1.10 g), and dry acetone (30 ml) was stirred for a period of 2 hours at the ambient temperature (ca 25° C.) and kept at that temperature for a further 18 hours. After diluting the mixture with diethyl ether (300 ml) the resultant mixture was washed with dilute aqueous sodium carbonate solution and dried over anhydrous magnesium sulphate. The solvents were evaporated and the residual oil purified by preparative thick layer chromatography using silica gel plates and chloroform eluent, to give 2-chloro-4-fluorobenzyl(±)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate (1.31 g) as a colourless oil.

Workup

  1. waitkept at that temperature for a further 18 hours
  2. washwas washed with dilute aqueous sodium carbonate solution
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvents were evaporated
  5. customthe residual oil purified by preparative thick layer chromatography

Sources & evidence

ORD record
ord-9140d3cea3a94b44a60ffea4e13edd27
Source dataset
uspto-grants-1986_01
Patent number
US04567199

Reaction notes

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