4-(BROMOMETHYL)PHENYLACETIC ACID

622-47-9

13737-36-5

The general procedure for the synthesis of 4-bromomethylphenylacetic acid from p-toluacetic acid was as follows: 24 g of p-toluacetic acid was added to 250 ml of hydrogen trichloride, followed by 75 ml of chlorobenzene as a solvent. To the reaction system, 30 g of N-bromosuccinimide (NBS) and 0.5 g of benzoyl peroxide were added as initiator. Mechanical stirring was turned on and the reaction was heated to 85°C and under incandescent light. The reaction temperature will automatically rise to 110 °C, at which point the reaction temperature needs to be controlled in the range of 90-110 °C. The reaction continues at this temperature for 8 hours, during which the progress of the reaction is monitored by TLC. Upon completion of the reaction, the reaction mixture is cooled and the solid product will precipitate. The solid is collected by filtration and the filter cake is washed with plenty of water. The filter cake was filtered to dryness as much as possible, resulting in 33.7 g of white solid product in 91.9% yield and 99.2% HPLC purity.