m-Chloroperbenzoic acid → Methyl 3-bromo-5-(oxiran-2-yl)benzoate

Participants

Reaction Steps

To a stirred solution of methyl 3-bromo-5-vinylbenzoate (1.00 g, 4.15 mmol) in CH2Cl2 (40 mL) at 0° C. was added m-chloroperbenzoic acid (70% purity, 1.43 g, 5.80 mmol) in portions over a 10 minute period. The mixture was warmed to room temperature and stirred for 2 hours upon which it was poured onto saturated sodium bicarbonate (250 mL). The mixture was extracted with ethyl acetate (3×100 mL) and the combined extracts were dried over Na2SO4 and concentrated. The residue was purified by column chromatography (0-50% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): 7.92 (t, 1H, J=1.7 Hz), 7.86 (t, 1H, J=1.5 Hz), 7.78 (t, 1H, J=1.7 Hz), 4.09 (q, 1H, J=2.5 Hz), 3.87 (s, 3H), 3.17-3.14 (m, 1H), 2.92-2.90 (m, 1H).

Provenance & Evidence