Sodium borohydride → (3-Bromopyridin-2-yl)methanol

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3-Bromo-pyridine-2-carboxylic acid methyl ester (12.8 g, 59.2 mmol) is dissolved in methanol (150 mL) and cooled to 0° C. To the mixture is added NaBH4 (11.2 g, 296 mmol) in 1.0 g portions. The mixture is warmed to room temperature and stirred for 3 h. The methanol is removed under reduced pressure, AcOEt is added and the solution is washed with saturated, aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure to yield 6.8 g (62%) of the title compound as a white solid. GCMS m/e 187 [M−H]−.

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