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

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-nicotinic acid methyl ester (example 26d) (10 g, 46.29 mmol) in anhydrous EtOH (100 ml) was cooled to 0° C. and NaBH4 (4.03 g, 106.47 mmol) was added in portions within 15 min. After stirred at 0° C. for 1 hour the ice bath was removed and stirring was continued at room temperature for 3 hours, then the reaction mixture was heated to reflux overnight. The solvent was evaporated and acetone (50 mL) was added and the solution stirred for 30 minutes then the acetone was evaporated. Saturated aqueous K2CO3 (50 mL) was added and the mixture was refluxed for 1 hour then diluted with water (100 mL) and extracted with DCM. The organic phase was dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (5% MeOH in DCM) to give 4.78 g of pure (5-bromopyridin-3-yl)methanol as a light yellow oil. Yield 55%. 1H NMR (400 MHz, CDCl3): 2.60 (t, 1H); 4.73-4.74 (d, 2H), 7.90 (s, 1H,), 8.47 (s, 1H), 8.57 (s, 1H).

Provenance & Evidence