Sodium borohydride → 6-Bromo-3-pyridinemethanol

To a solution of 2-bromo-5-pyridinecarboxaldehyde (1 Scheme 27, 9.3 g, 50 mmol) in EtOH (300 mL) was added sodium borohydride (3.7 g, 100 mmol) portion-wise for 10 min at room temperature. After further stirring for 30 min, excess sodium borohydride was quenched by slow addition of acetone (10 mL) to the reaction mixture. The solvent was evaporated and the residue was extracted with ethyl acetate/brine. The organic layer was dried (Na2SO4) and concentrated to afford a colorless oil (8.5 g, 90%); 1H NMR (300 MHz, CDCl3) δ 4.58 (bs, OH, 1 H), 4.62 (s, 2 H), 7.40 (d, J=8.40, 1 H), 7.54 (dd, J=7.2, 1.2 Hz, 1 H), 8.20 (s, 1 H); 13C NMR (75 MHz, CDCl3) 61.5, 128.3, 136.6, 138.0, 140.6, 148.6. HRMS (EI) calcd for C6H6BrNO 186.9632 and 188.9613, found 186.9629 and 188.9663.

1. customexcess sodium borohydride was quenched by slow addition of acetone (10 mL) to the reaction mixture
2. customThe solvent was evaporated
3. extractionthe residue was extracted with ethyl acetate/brine
4. dry with materialThe organic layer was dried (Na2SO4)
5. concentrationconcentrated

ORD record

ord-3ad37b67d66e4b428f5bb9f49a384ff4

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06416861B1