Synthesis
To a 250 mL round bottom flask was added 3-(4-bromophenyl)propionic acid (5 g, 21.83 mmol, 1.00 equiv) and methanol (50 mL). Thionyl chloride (7.76 g, 65.23 mmol, 5.30 eq.) was added slowly and dropwise with stirring. The reaction mixture was stirred at 70 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of a water/ice mixture. The aqueous phase was extracted with ethyl acetate (200 mL × 3), the organic phases were combined, washed sequentially with brine (100 mL × 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether:ethyl acetate (5:2, v/v) as eluent to afford methyl 4-bromo-3-phenylpropionate (4.84 g, 91% yield) as a colorless oil.
