Benzyl Bromide → 4-(1-Benzyloxy-ethyl)-3,5-dibromo-pyridine

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 1-(3,5-dibromo-pyridin-4-yl)-ethanol (600 mg, 1.4 mmol) in DMF (12 mL) is added sodium hydride (60% dispersion in mineral oil, 60 mg, 1.5 mmol). After stirring at 0° C. for 30 min, benzyl bromide (281 mg, 1.6 mmol) is added. The reaction is warmed and stirred at room temperature for 16 h. The reaction is quenched with the addition of saturated aqueous NH4Cl and H2O and is extracted with EtOAc. The combined organic layers are dried and concentrated. The crude product is purified by flash column chromatography to provide 306 mg of 4-(1-benzyloxy-ethyl)-3,5-dibromo-pyridine.

Provenance & Evidence