Sodium borohydride → (5-Bromo-4-chloropyridin-3-yl)methanol

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Reaction Steps

5-Bromo-4-chloro-pyridine-3-carbaldehyde (500 mg, 2.27 mmol) is dissolved in MeOH (20 mL) and sodium borohydride (257 mg, 6.80 mmol) is added. The mixture is stirred for 1 hr at room temperature and the solvent is removed in vacuo. Then saturated NH4Cl aqueous solution (20 mL), water (50 mL) and EtOAc (50 mL) are added and the mixture is stirred for 10 min. The aqueous layer is separated and extracted with EtOAc (2×50 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 400 mg of (5-bromo-4-chloro-pyridin-3-yl)-methanol.

Provenance & Evidence