Pentafluorobenzyl bromide → Pentafluoro-benzyl 2,2-dimethyl-3-(2-chloro-2-p-chloro-phenyl-vinyl)-cyclopropanecarboxylate

HRID 905247Notes

Reaction equation

HRID 905247 reaction equation
[K].[CH3:2][C:3]1([CH3:19])[CH:5]([CH:6]=[C:7]([Cl:15])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:4]1[C:16]([OH:18])=[O:17].[F:20][C:21]1[C:26]([CH2:27]Br)=[C:25]([F:29])[C:24]([F:30])=[C:23]([F:31])[C:22]=1[F:32]>CN(C)C=O>[CH3:2][C:3]1([CH3:19])[CH:5]([CH:6]=[C:7]([Cl:15])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:4]1[C:16]([O:18][CH2:27][C:26]1[C:25]([F:29])=[C:24]([F:30])[C:23]([F:31])=[C:22]([F:32])[C:21]=1[F:20])=[O:17]

Participants

5

Reactant 3

HCID 74484Pentafluorobenzyl bromideHCID 5462222PotassiumHCID 54156496HCID 54156496, compound

Product 1

HCID 131713325Pentafluoro-benzyl 2,2-dimethyl-3-(2-chloro-2-p-chloro-phenyl-vinyl)-cyclopropanecarboxylateYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.7 g (0.033 mol) of the potassium salt of 2,2-dimethyl-3-(2-chloro-2-p-chlorophenyl-vinyl)-cyclopropanecarboxylic acid were dissolved in 100 ml of dimethylformamide and the solution was heated to 120° C., together with 6.8 g (0.026 mol) of pentafluorobenzyl bromide, for 3 hours. After the reaction had ended, the dimethylformamide was distilled off in vacuo and the residue which remained was taken up in 200 ml of methylene chloride. The methylene chloride solution was then extracted by shaking twice with 100 ml of water each time, the organic phase was dried over sodium sulphate and the solvent was stripped off in vacuo. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 9.0 g (74.4% of theory) of pentafluoro-benzyl 2,2-dimethyl-3-(2-chloro-2-p-chloro-phenyl-vinyl)-cyclopropanecarboxylate were obtained as a yellow oil with the refractive index nD25 :1.5382.

Workup

  1. distillationthe dimethylformamide was distilled off in vacuo
  2. extractionThe methylene chloride solution was then extracted
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

Sources & evidence

ORD record
ord-93692779fc2842c4921ffe45406ef841
Source dataset
uspto-grants-1983_12
Patent number
US04423066

Reaction notes

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