Bromine → 2-Bromo-4-(methylsulfonyl)phenol

Participants

Reaction Steps

A solution of bromine (0.9 ml, 17.45 mmol) in glacial acetic acid (10 ml) was added dropwise to a stirred solution of 4-(methanesulfonyl)phenol (Description 26; 3 g, 17.45 mmol). The resulting solution was stirred at ambient temperature for 16 h. Bromine (0.45 ml) in glacial acetic acid (5 ml) was added dropwise and the solution was stirred for 2 h. The excess acetic acid and bromine were removed in vacuo and the residue was azeotroped with toluene to give the desired compound as an off-white solid (3.54 g, 81%). 1H NMR (250 MHz, CDCl3) δ8.06-8.05 (1H, d, J 2.3 Hz), 7.73-7.69 (1H, dd, J 8.6, 2.3 Hz), 7.06-7.02 (1H, d, J 8.6 Hz), and 3.06 (3H, s).

Provenance & Evidence