m-Chloroperbenzoic acid → 5-Bromo-2-methoxyphenol

Participants

Reaction Steps

To a solution of 5-bromo-2-methoxybenzaldehyde (2.4 g, 11.2 mmol) in 50 mL CH2Cl2, m-chloroperbenzoic acid (70-75%, 7 g, 28.4 mmol pure m-CPBA,) was added and the mixture was stirred at ambient temperature for 2 days. The reaction was quenched with aqueous saturated NaHCO3 solution and extracted with ethyl acetate (50 mL×3). The organic extract was dried with anhydrous sodium sulfate and filtered through a silica gel bed. Evaporation of the solvent gave compound 35 (2.1 g) in 92% yield; mp 62-64° C.; 1H NMR (CDCl3) δ3.87 (3H, s), 6.71 (1H, d, J=8.6), 6.97 (1H, dd, J1=8.6, J2=2.4), 7.07 (1H, d, J=2.4); 13C NMR δ56.59, 112.36, 113.75, 118.33, 123.29, 146.37, 146.98.

Provenance & Evidence