Triphenylphosphine dibromide → 1-(4-(Bromomethyl)phenyl)propan-2-one

Participants

Reaction Steps

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (3.15 g) and dibromotriphenylphosphorane (8.11 g) was refluxed in acetonitrile (50 ml) for 1 hour. The solvent was removed and the residue chromatographed on silica. Elution with ether gave 1-(4-bromomethylphenyl)propan-2-one, 3.4 g. τ(CDCl3) 7.92 (3H, s), 6.4 (2H, s), 5.6 (2H, s), 2.9 (2H, d, J=8 Hz), 2.65 (2H, d, J=8 Hz). This was ketalised in an analogous manner to that described in Description 2 to give the title compound, 3.73 g. τ(CDCl3) 8.7 (3H, s), 7.1 (2H, s), 5.9-6.3 (4H, m), 5.54 (2H, s), 2.75 (4H, s).

Provenance & Evidence