3-Acetyl-5-bromopyridine → 3-Bromo-5-(1-hydroxyethyl)pyridine

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Reaction Steps

1-(5-Bromo-pyridin-3-yl)-ethanone (3.0 g, 15 mmol) is dissolved in MeOH (20 mL) and sodium borohydride (1.1 g, 30 mmol) is added in 5 small portions every 15 min. The mixture is stirred for 16 hrs and the solvent is then removed in vacuo. Saturated aqueous NH4Cl solution (10 mL) is added along with 30 mL of water. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 2.9 g of 1-(5-bromo-pyridin-3-yl)-ethanol.

Provenance & Evidence