Triphenylphosphine → (1S,2S,5S)-2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Participants

Reaction Conditions

Reaction Steps

15.6 g triphenylphosphine were dissolved in 300 ml acetonitrile, and 3.02 ml bromine were added to the solution in drops with vigorous stirring at a temperature of 0° C. Then a solution of 10 g cisdihydronopol (=2-((1S,2S,5S)6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethanol) in 100 ml acetonitrile was added, and the reaction mixture was heated to 100° C. (bath temperature) for 5 hours. The reaction mixture was worked up by distilling off the solvent under reduced pressure, and the residue was purified chromatographically over silica gel using dichloromethane as eluent. 12.0 g 2-((1S,2S,5S)-6,6dimethylbicyclo[3,1,1]hept-2-yl)-ethyl bromide were obtained.

Provenance & Evidence