Carbon tetrabromide → HCID 22279681, compound

Participants

Reaction Steps

A dichloromethane solution (120 ml) of triphenylphosphine (57.7 g, 0.22 mol) in an ice bath were added dropwise to the dichloromethane solution (120 ml) including carbon tetrabromide (36.5 g, 0.11 mol) under a nitrogen atmosphere. After the end of dropping, the reaction mixture was stirred for 5 more minutes. To the reaction solution in the ice bath was added dropwise under a nitrogen atmosphere a dichloromethane solution (90 ml) of the crude 3-cyclohexyloxypropionaldehyde (8.6 g) obtained above, and after dropping, the reaction mixture was stirred for 25 more minutes. The reaction solution was diluted with dichloromethane, and washed with a saturated aqueous sodium hydrogencarbonate solution and then with a saturated aqueous sodium chloride solution. After the dichloromethane layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=100:1-33:1) to afford 4-cyclohexyloxy-1,1-dibromobut-1-ene (12.6 g, 55% yield, 2 processes).

Provenance & Evidence