5-Bromo-2-hydroxybenzonitrile

1761-61-1

40530-18-5

Synthesis of 5-bromo-2-hydroxybenzonitrile: To a solution of 5-bromosalicylaldehyde (80.0 g, 0.40 mol) in formic acid was added hydroxylamine hydrochloride (36.0 g, 0.52 mol) and sodium form (37.0 g, 0.52 mol) in sequence. The reaction mixture was stirred at 100 °C for 7 hours. After completion of the reaction, the solvent was removed by evaporation and the residue obtained was dissolved in ethyl acetate. The organic layer was washed with water and dried. The solvent was again removed by evaporation and petroleum ether was added to the residue, and the precipitated crystals were filtered to give 5-bromo-2-hydroxybenzonitrile (75.2 g, 95% yield).1H-NMR (DMSO-d6) δ: 6.98 (d, J = 8.9 Hz, 1H), 7.65 (dd, J = 8.9,2.4 Hz, 1H), 7.86 (d, J = 2.4 Hz , 1H), 11.41 (s, 1H).