Carbon tetrabromide → 4-Bromomethylphthalic acid dimethyl ester

Participants

Reaction Steps

36 g (176 mmol) of dimethyl 4-hydroxymethylphthalate are dissolved in 300 mL of dichloromethane and 70 g (211 mmol) of tetrabromomethane are added. A solution of 55.3 g (211 mmol) of triphenylphosphine in 200 mL of dichloromethane is then added slowly and the reaction mixture is stirred for 3 h at room temperature. After treatment with water and extraction with dichloromethane, the residue is purified by chromatography on a column of silica (eluent: dichloromethane). The desired product is obtained in the form of a colourless oil (m=25 g; Y=50%).

Provenance & Evidence