Benzyl Bromide → 3-Benzyl 1-methyl 4-hydroxyisophthalate

Participants

Reaction Steps

To a solution of 2-hydroxy-5-(methoxycarbonyl)benzoic acid (4.0 g, 20.4 mmol) in DMF (40 mL) was added KHCO3 (2.04 g, 20.4 mmol) and benzyl bromide (3.49 g, 20.4 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 20 h. The reaction mixture was diluted with water, extracted with EtOAc (2×) and the combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. The crude material was purified by flash chromatography (gradient from 0% to 30% EtOAc/hexanes) to provide the title compound (5.3 g, 92%) as an off-white solid. 1H NMR (CDCl3) δ 11.21 (s, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.11 (dd, J=8.8, 2.4 Hz, 1H), 7.47-7.37 (m, 5H), 7.01 (d, J=8.8 Hz, 1H), 5.42 (s, 2H), 3.89 (s, 3H); MS(ESI−) m/z 285.2 (M−H)−.

Provenance & Evidence