Heptane → Triphenylphosphine Oxide

Participants

Reaction Conditions

Reaction Steps

Triphenyl phosphine (5.84 g, 22.3 mmol) was added to a solution of (5-tert-butyl-2-methoxyphenyl)methanol (4.20 g, 21.8 mmol) in anhydrous DCM (80 ml) and the mixture cooled to 10° C. Carbon tetrabromide (7.39 g, 22.3 mmol) was added with stirring over 10 min, and after 30 min the temperature was raised to ambient temperature. Stirring continued for 17.5 h when the solvent was lowered to 20 ml under reduced pressure. Addition of heptane (80 ml) with stirring resulted in precipitation of triphenyl phosphine oxide, which was removed by filtration of the mixture through dicalite. Evaporation of the filtrate gave a straw coloured gum, purification of which was achieved by chromatography on silica using heptane:DCM (1:1) as eluent to afford 2-bromomethyl-4-tert-butyl-1-methoxybenzene as a clear gum (2.02 g, 36%).

Provenance & Evidence