5-bromo-2-pyridinecarboxylic acid, methyl ester (648mg, 3mmol) in 10ml of methanol was slowly added to sodium borohydride (340mg, 9mmol) in an ice bath. After that, the ice bath was removed and the reaction mixture was warmed to room temperature. The reaction was stirred for 12 hours. Then 1N HCl was added to adjust the pH to 1. Afterward, a saturated sodium bicarbonate solution was added to adjust the pH to 8. The mixture was then extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. This resulted in the formation of 535mg of white solid, which was identified as 5-bromo-2-pyridinemethanol. The yield of the desired product was 94.8%.
