Triphenylphosphine → 4-Acetoxy-2-bromomethylbutyl acetate

Participants

Reaction Steps

A solution of 4-acetoxy-2-hydroxymethylbutyl acetate (11.04 g, 0.054 mol) and triphenylphospine (21.27 g, 0.081 mol) in dry dichloro methane (150 ml) was stirred at 0° C., and N-bromo-succinimide (14.43 g, 0.081 mol) was added in portions. The mixture was kept at 0° C. for 20 h, evaporated to small volume and stirred with 50 ml of ethyl acetate+n-hexane (1+1). the white triphenylphospine oxide was filtered off and washed with a little ethyl acetate+n-hexane (1-1). The combined filtrate was evaporated and purified on a 200 g SiO2 column with ethyl acetate+n-hexane (1+1) as eluent. The 250 -550 ml fraction was evaporated in vacuum to give 11.90 g (82%) of pure 4-acetoxy-2-bromomethylbutyl acetate. TLC on silica (ethyl acetate+n-hexane 1+1): Rf 0.59.

Provenance & Evidence