Iodoethane → 3-Bromo-5-ethoxypyridine

Participants

Reaction Steps

A solution of 5-bromopyridin-3-ol (70 g, 402 mmol), K2CO3 (111 g, 805 mmol) and iodoethane (69.0 g, 443 mmol) in DMF (700 mL) was stirred for 16 h at 25° C. Then the mixture was concentrated to give the residue which was extracted with DCM (2×200 mL), dried over Na2SO4, filtered, and concentrated to give 3-bromo-5-ethoxypyridine (53 g, 218 mmol, 54.2% yield): NMR (400 MHz, CD3OD) δ 8.19-8.17 (m, 2H), 7.60-7.59 (m, 1H), 4.13-4.07 (m, 2H), 1.40 (t, J=7.0 Hz, 3H); ES-LCMS m/z 202 (M+H).

Provenance & Evidence