Ethyl 5-bromopyridine-3-carboxylate → (5-Bromo-3-pyridinyl)methanol

Participants

Reaction Steps

Crushed pellets of sodium borohydride were added over 30 minutes to a solution of 5-bromonicotinic acid ethyl ester of Step A (5.0 g, 21.7 mmol) in ethanol (150 mL). The reaction was stirred at room temperature for five days and then quenched with water. The ethanol was removed under reduced pressure and the aqueous residue was extracted three times with methylene chloride. The combined organics were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a yellow oil. The material was purified by flash chromatography over silica gel Marck-60 using 2:1 hexane/ethyl acetate as an eluant to give the title compound (1.41 g) as a light yellow liquid which was used in the next step without further purification.

Provenance & Evidence