Water → 2-Bromo-1-methoxy-4-(methylsulfonyl)benzene

Participants

Reaction Steps

Potassium carbonate (2.31 g, 16.8 mmol) was added to a solution of 2-bromo-4-(methanesulfonyl)phenol (Description 27; 3.5 g, 14 mmol) in dimethylformamide (50 ml). The resulting solution was stirred for 30 min. and methyl iodide (1.04 ml, 16.8 mmol). After stirring for 1 h. the solution was poured into water (200 ml) and extracted with ethyl acetate (2×100 ml). The combined organics were washed with water and dried over sodium sulphate. Removal of the solvent in vacuo gave a white solid which was crystallised from diethyl ether to give the title compound (2.02 g). 1H NMR (250 MHz, CDCl3) δ8.12-8.11 (1H, d, J 2.2 Hz), 7.90-7.86 (1H, dd, J 8.7, 2.2 Hz), 7.04-7.00 (1H, d, J 8.7 Hz), and 3.99 (3H, s), and 3.05 (3H, s).

Provenance & Evidence