2-Bromo-2-phenylacetic acid

• Polymandelide by reacting with triethylamine.
• α-Mercaptophenylacetic acid by treating with sodium hydrosulfide (NaSH·H₂O).
• β-Lactams by reacting with imines in the presence of triphenylphosphine as a mediator.

103-82-2

4870-65-9

General procedure for the synthesis of α-bromophenylacetic acid from phenylacetic acid: 2-phenylacetic acid (376 mg, 2.7 mmol), N-bromosuccinimide (540 mg, 3.05 mmol), and carbon tetrachloride (5.5 mL) were added to a dry two-necked flask fitted with a condensing unit. Azobisisobutyronitrile (23 mg, 0.14 mmol) was added with stirring and the reaction was heated to reflux at 77°C with stirring for 2 hours. The progress of the reaction was monitored by nuclear magnetic resonance spectroscopy (1H NMR) until 2-phenylacetic acid was completely consumed. Upon completion of the reaction, the reaction was cooled naturally to room temperature, and the reaction mixture was diluted with hexane (10.0 mL) and filtered. The solvent was removed by rotary evaporation and purified by silica gel column chromatography (eluent: n-hexane/ether, 2:1, v/v) to afford α-bromophenylacetic acid as a white solid (95% yield).