Methanol → Methyl 2-(4-bromophenyl)acetate

Participants

Reaction Steps

A solution of 202.78 g 4-bromophenylacetic acid in 1.5 L methanol was treated with 15 mL concentrated sulfuric acid and the resulting mixture refluxed under nitrogen for 3 hours. Almost all of the methanol was removed by distillation. Dilute the residue with 1 L ether. Separate the bottom layer and extract that with 2×100 mL ether. Wash the combined ether solution with 3×250 mL 5% NaHCO3 and 250 mL saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give a crude product as light tan oil. Filter that through 300 g silica gel with 10% EtOAc in hexanes and concentrated under reduced pressure to give the title compound as colorless oil. 1H NMR (CDCl3, 500 MHz) δ 7.46˜7.48 (m, 2H), 7.16˜7.19 (m, 2H), 3.72 (s, 3H), 3.60 (s, 2H).

Provenance & Evidence