960298-00-4

128071-98-7

100-51-6

960298-00-4

4-Bromo-2-fluoropyridine (5.28 g, 30 mmol) and benzyl alcohol (3.24 g, 30.00 mmol) were dissolved in anhydrous tetrahydrofuran (THF, 50 mL) under argon protection. The reaction system was cooled to 0 °C in an ice-water bath. Potassium tert-butoxide (3.37 g, 30.00 mmol) was added slowly over 20 min with vigorous stirring, approximately 100 mg at a time. after addition, the reaction was continued at 0 °C for 60 min with stirring. Subsequently, the ice water bath was removed and the reaction mixture was warmed to room temperature and stirring was continued for 30 min. Upon completion of the reaction, water (5 mL) was added to the mixture and most of the THF was evaporated under reduced pressure. the residue was extracted by partitioning with pentane (75 mL) and water (50 mL). The organic phase was separated, washed with water (2 x 25 mL) and dried over anhydrous magnesium sulfate (MgSO4). The solvent was removed by concentration under reduced pressure to give the title compound 2-(benzyloxy)-4-bromopyridine 7.86 g in 99% yield. The product was characterized by 1H NMR (500 MHz, DMSO-d6): δ 8.10 (d, 1H), 7.44 (d, 2H), 7.38 (t, 2H), 7.33 (t, 1H), 7.25 (d, 1H), 7.20 (s, 1H), 5.36 (s, 2H).