Benzyl Bromide → HCID 57421820, compound

Participants

Reaction Steps

To a stirred solution of methyl 5-hydroxynicotinate (8.5 g, 55.6 mmol) and K2CO3 (11.5 g, 83.3 mmol) in DMF (20 mL) at 0° C. was added (bromomethyl)benzene (8 mL, 66.7 mmol) drop wise over 5 min. The resulting mixture was stirred at room temperature for 2 hours. The mixture was quenched with water (100 mL) and extracted with EA (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1) to give methyl 5-(benzyloxy)nicotinate (4 g, 30.7%) as a yellow oil.

Provenance & Evidence