Sodium borohydride → (4-Bromopyridin-2-yl)methanol

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Sodium borohydride (763 mg, 20.17 mmol) was added portionwise to a solution of 4-bromo-pyridine-2-carboxylic acid methyl ester (1.98 g, 9.166 mmol) in ethanol (50 mL) under nitrogen and the reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by the addition of acetone (10 mL) and the reaction was stirred for 15 minutes. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organics were collected, dried over anhydrous sodium sulfate and the solvent evaporated to afford the title compound (1.61 g, 94%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ3.4-3.5 (br s, 1H), 4.80 (s, 2H), 7.40 (dd, J=5.4, 1.8 Hz, 1H), 7.50 (br m, 1H), 8.39 (d, J=5.4 Hz, 1H). LCMS (m/z) 188/200 [M+H], Tr=1.55 min.

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