Water → cis-3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid

HRID 370572Notes

Reaction equation

HRID 370572 reaction equation
[Br:1][C:2](Br)([Br:12])[CH:3]1[CH:8]2[CH:6]([C:7]2([CH3:10])[CH3:9])[C:5](=[O:11])[O:4]1.O>C(O)(=O)C.CCOCC.[Zn]>[Br:1][C:2]([Br:12])=[CH:3][C@@H:8]1[C@H:6]([C:5]([OH:11])=[O:4])[C:7]1([CH3:9])[CH3:10]

Participants

6

Reactant 2

HCID 962WaterHCID 125252254-Tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane

Product 1

HCID 12525241cis-3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a chilled suspension of zinc powder (0.494 g, 0.0076 mole) in 0.57 ml of acetic acid and 3 ml of ether was added dropwise over a period of 20 minutes a solution of 4-tribromomethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane (0.72 g, 0.0019 mole) in 5 ml of ether. The mixture was stirred at 0° for one hour. After adding 30 ml of ether and 5 ml of water, the mixture was filtered through Celite filter aid. The organic layer was separated, washed three times with saturated aqueous sodium chloride, dried magnesium sulfate, and the ether was removed by evaporation to give crystalline cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid (0.489 g, 86% yield); mp, 112°-114° after recrystallization from n-hexane.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. filtrationfilter aid
  3. customThe organic layer was separated
  4. washwashed three times with saturated aqueous sodium chloride, dried magnesium sulfate
  5. customthe ether was removed by evaporation

Sources & evidence

ORD record
ord-384c86e0e36d4244b56d0ee5e2c8db6d
Source dataset
uspto-grants-1985_07
Patent number
US04526987

Reaction notes

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