3-bromo-5-hydroxypyridine is an important industrial raw material widely used in medicine, pesticides, dyes, and other industries. Since the pyridine ring has biological activity and plays an irreplaceable role in synthesising drugs that cannot be replaced by other groups or functional groups, it is a hot area in pharmaceutical research. The hydroxyl and bromine atoms in the structure of 3-bromo-5-hydroxypyridine have diverse chemical reactivity. The alcohol hydroxyl unit in its structure can undergo nucleophilic substitution reactions with common alkyl halides under alkaline conditions to obtain corresponding ether derivatives.
5-Bromo-3-methoxypyridine was refluxed with 20 mL (57%) of hydrogen bromide for 24 hours. The reaction was quenched with saturated sodium bicarbonate solution and the base mixture was extracted with 3 × 50 mL of dichloromethane. The organic fractions were pooled, dried (magnesium sulfate), filtered, and evaporated to give a white solid (3 g, >95% purity) identified as 3-bromo-5-hydroxypyridine by thin layer chromatography.
