Benzyl Bromide → 3-(Benzyloxy)-2-chloropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloropyridin-3-ol (16.3 g, 125 mmol) and K2CO3 (24.3 g, 176 mmol) in acetone (150 ml) was added dropwise (bromomethyl)benzene (17.9 ml, 151 mmol). The mixture was stirred overnight at 50° C. and then concentrated to dryness. Water (100 ml) was added and the mixture extracted with CH2Cl2. The organics were dried over Na2SO4, and concentrated to a crude residue that was dissolved in 20 ml CH2Cl2. Et2O (250 ml) was added and then the solvent was decanted from the residue. The residue was then purified on a silica gel plug by eluting with 25% EtOAc/Hexanes to give 3-(benzyloxy)-2-chloropyridine (22.3 g, 80% yield) as a solid.

Provenance & Evidence