Benzyl Alcohol → 2-Benzyloxy-5-bromopyridine

Participants

Reaction Steps

To a solution of benzyl alcohol (11.4 g, 0.105 mol) in N,N-dimethylformamide (250 ml) was added 70% oily sodium hydride (4.2 g, 0.123 mol) at 0° C., followed by stirring as it was for 1.5 hours. Then, 2,5-dibromopyridine (25 g, 0.106 mol) was added thereto, followed by stirring at 70° C. for 2 hours. After cooling as it was, the reaction mixture was diluted with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with a saturated aqueous ammonium chloride solution twice, dried over anhydrous magnesium sulfate and concentrated, to give a crude product of the title compound (29.5 g) as a pale yellow liquid.

Provenance & Evidence