3-Bromo-2-chloro-5-methylpyridine → 3-Bromo-2-ethoxy-5-methylpyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100° C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

Provenance & Evidence