Ethyl 4,6,6-tribromo-3,3-dimethylhex-5-enoate → Ethyl 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1763980Notes

Reaction equation

HRID 1763980 reaction equation
[CH3:1][C:2]([CH3:15])([CH:9](Br)[CH:10]=[C:11]([Br:13])[Br:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[CH:9]([CH:10]=[C:11]([Br:13])[Br:12])[CH:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 1

HCID 13321424Ethyl 4,6,6-tribromo-3,3-dimethylhex-5-enoate

Product 1

HCID 12550018Ethyl 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

4.1 Parts of the so obtained ethyl 3,3-dimethyl-4,6,6tribromo-5-hexenoate was dissolved in 35 parts of dry benzene, and 1.9 parts of sodium t-butylate was added to the solution and the mixture was agitated for 1 hour under reflux of benzene. The liquid reaction mixture was poured into ice water and extracted with diethyl ether, and ether and benzene were distilled from the organic layer. The residue was subjected to distillation under reduced pressure to obtain 3.2 parts of ethyl 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropane-carboxylate having a boiling point of 92° - 94° C. under 0.5 mm Hg. The yield was 98%.

Workup

  1. additionwas added to the solution
  2. customThe liquid reaction mixture
  3. extractionextracted with diethyl ether, and ether and benzene
  4. distillationwere distilled from the organic layer
  5. distillationThe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-9d84dcb51278431f8aa5ee64a5915ae3
Source dataset
uspto-grants-1978_09
Patent number
US04113968

Reaction notes

Loading…