3-Bromo-2-hydroxy-6-methoxybenzoic acid → 2-Bromo-5-methoxyphenol

Participants

Reaction Steps

3-Bromo-2-hydroxy-6-methoxybenzoic acid [T. de Paulis el. al., J. Med. Chem., (1985), 28, 1263-1269] (5 g, 0.02 mol) was heated in quinoline (200 mL) at 160° C. for 1 h. On cooling, the product was partitioned between Et2O and 3M HCl. The organic extract was washed with water and brine then dried (MgSO4), filtered and evaporated to give the title compound which was recrystallized from 5% ethyl acetate/hexane (4 g, 97%); m.p. 40°-42° C. Anal. Calc. for C7H7 BrO2 : C, 41.41; H, 3.48. Found C, 41.39; H, 3.37.

Provenance & Evidence