General procedure for the synthesis of 3-bromopyridine-4-methanol from 3-bromopyridine-4-aldehyde: To a solution of 3-bromo-4-pyridinecarboxaldehyde (3.0 g, 16.2 mmol) in anhydrous methanol (40 mL) was slowly added NaBH4 (0.736 g, 19.5 mmol) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 2 h under nitrogen protection. After completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, water and ethyl acetate were added for extraction, and the organic layer was separated and washed with distilled water, dried over anhydrous Na2SO4, and finally concentrated under reduced pressure to obtain the target product 3-bromopyridine-4-methanol (3.021 g, 100% yield) as a white powder. The structure of the product was determined by 1H NMR (CDCl3, 300 MHz, 298K, δ ppm): 8.61 (s, 1H), 8.51 (d, 1H, J = 4.8 Hz), 7.55 (d, 1H, J = 4.8 Hz), 4.76 (s, 2H), 2.89 (s, 1H); 13C NMR (CDCl3, 75.5MHz, 298K, δ ppm) 298K, δ ppm): 151.14, 149.45, 148.54, 122.47, 119.90, 63.47; GC/MS (m/z): 188; IR (KBr, v, cm-1): 3152, 2894, 2829, 1593, 1447, 1401, 1333, 1223, 1170. 1070, 1024, 834, 705, 599 Confirmed.
