2-Bromophenol → 2-Bromo-6-nitrophenol

Participants

Reaction Steps

2-Bromophenol (50.0 g, 0.29 mol) was added slowly to a cold (10° C.) solution of sodium nitrate (36.9 g, 0.43 mol) in conc. sulfuric acid (79 g) and water (100 mL) and the resulting mixture was allowed to stir at room temperature for 2 h. Water (400 mL) was added and the resulting mixture was extracted with diethyl ether and the extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane). The partly purified product was triturated with hexane to afford the title compound (19.2 g, 30%) as a bright, yellow solid. 1H NMR (300 MHz, CDCl) δ 11.10 (S, 1h), 8.13 (d, J=7.9 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 6.90 (t,J=7.9 Hz, 1H).

Provenance & Evidence