Hydrochloric Acid → (5-Bromo-3-pyridinyl)methanol

Participants

Reaction Steps

To a solution of 5-bromonicotinic acid (20.00 g, 97.00 mmol) in anhydrous THF (250 mL) was added a solution of BH3 (1 M in THF, 197 mL) slowly at rt over a period of 1 h. The reaction mixture was stirred for 1 h at rt and then was heated at reflux temperature for 5 h. The reaction mixture was cooled to rt and treated with 1 M HCl (100 mL) drop-wise. The resulting mixture was stirred for 1 h and treated with 10% aq. NaOH until pH 10. The solution was then extracted with ethyl acetate (4×200 mL). The combined organic extracts were washed with H2O, dried over anhydrous Na2SO4, filtered and concentrated to yield the crude alcohol (10.71 g). Purification of the crude compound (SiO2: 0-5% 2 M NH3 in MeOH/DCM) gave (5-bromo-pyridin-3-yl)-methanol (4.14 g, 22%).

Provenance & Evidence