Bromine → 3-Bromo-6-chloropyridin-2-amine

Participants

Reaction Steps

6-Chloro-pyridin-2-ylamine (5 g, 38.89 mmol) is dissolved in chloroform (250 mL) and a solution of bromine (1.33 mL, 26 mmol) in chloroform (50 mL) is slowly added over a one hour period. During the addition a precipitate (hydrobromide salt of the starting material) forms. After stirring overnight the reaction mixture is filtered, the filtrate is evaporated and the residue is partitioned between ethyl acetate and 1 M sodium carbonate solution. The organic phase is separated, evaporated and the solid residue purified by flash chromatography (silica gel, 15% ethyl acetate in petroleum ether) affording the title compound (1.44 g, 17%) as a solid. The material is carried through the next three reaction steps.

Provenance & Evidence