Benzyl Bromide → 5-(Benzyloxy)-2-bromopyridine

Participants

Reaction Steps

11.1 2-Bromo-5-hydroxypyridine (2 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min, benzylbromide (1.1 eq.) is added and the reaction stirred 16 h at RT. The reaction solution is diluted with water and extracted with methyl tert.-butyl ether. The combined organic layers are dried over Na2SO4 and the solvent removed in vacuo. 5-Benzyloxy-2-bromo-pyridine is obtained after column chromatography (heptan/ethyl acetate) as a colourless powder in a yield of 64%; HPLC (method C): 2.09 min; LC-MS (method A): 1.987 min, 263.95 (M+H+).

Provenance & Evidence