Triphenylphosphine → HCID 11010750, compound

Participants

Reaction Conditions

Reaction Steps

An acetonitrile solution (100 ml) of triphenylphosphine (18.6 g, 70.9 mmols) was stirred at 0° C. Bromine (11.4 g, 3.7 ml, 71.3 mmols) was slowly blended into the solution. To the mixture, an acetonitrile (30 ml) solution of (E)-3-methyl-2-dodecen-1-ol (3′) was added dropwise, followed by stirring for 2 hours at 0° C. The solvent was removed under vacuum, and the residue was dissolved in dichloromethane. The solution was washed with saturated sodium bicarbonate and a saturated aqueous solution of sodium chloride, then dried over sodium sulfate, and concentrated. Pentane was added to the residue, and a solid formed was removed by filtration. The filtrate was concentrated in a vacuum to obtain 17.9 g (97%) of (E)-1-bromo-3-methyl-2-dodecene (4′).

Provenance & Evidence