Ethanol → Ethyl 5-bromo-4-methylnicotinate

Participants

Reaction Steps

To a stirred light brown suspension of 5-bromo-4-methylnicotinic acid (10.00 g, 46.3 mmol) and ethanol (2.97 mL) in DCM (231 mL) at 0° C. under argon was added EDCI (10.9 g, 55.5 mmol) and DMAP (566 mg, 4.63 mmol); stirring was continued overnight and the reaction mixture was allowed to warm up to room temperature. The reaction mixture was then poured on aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. 10% KH2PO4, with sat. NaHCO3 and with aq. sat. NaCl solution. The combined organic phases were dried (Na2SO4), filtered and evaporated to afford the title compound (9.49 g, 84%) as brown solid. MS: 244.0 (M+H+, 1Br).

Provenance & Evidence