Azobisisobutyronitrile → Methyl 4-acetoxy-3-bromomethyl-5-methylbenzoate

Participants

Reaction Steps

A solution of methyl 4-acetoxy-3,5-dimethylbenzoate (2.4 g) in carbon tetrachloride (35 mL) was treated with AIBN (azobisisobutrylnitrile, 0.177 g, 0.1 equivalent) and NBS (N-bromosuccinimide, 2.117 g, 1.1 equivalents). The reaction was heated at reflux under a nitrogen atmosphere for 6 h. The reaction was cooled to room temperature and diluted with chloroform (30 mL). This solution was washed with water (4×50 mL) and then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. An off-white, waxy solid was recovered. Yield=4.63 g. The crude bromide was used as such for the following reaction.

Provenance & Evidence