Thionyl Chloride → HCID 86094445, compound

Participants

Reaction Steps

To a mixture of (6-bromopyridin-2-yl)(6-methoxypyridin-2-yl)methanol (5.11 g, 17.31 mmol) in CH2Cl2 (56 mL) @ 0° C. under N2 was added SOCl2 (3.09 g, 25.97 mmol). The mixture was then allowed to warm to rt and stirred for 3 hr. The mixture was then cooled back to 0° C. and quenched with saturated aqueous sodium bicarbonate. The resulting mixture was extracted 3× with CH2Cl2. The combined organics were dried (Na2SO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (25-35% CH2Cl2 in Hexanes) to give 2-bromo-6-[chloro(6-methoxypyridin-2-yl)methyl]pyridine. 1H NMR (500 MHz, CDCl3) δ 7.76 (d, 1H, J=7.8), 7.61-7.54 (m, 2H), 7.41 (d, 1H, J=7.8), 7.12 (d, 1H, J=7.1), 6.66 (d, 1H, J=8.3), 6.02 (s, 1H), 3.86 (s, 3H), LRMS m/z (M+H) Calcd.: 313.0, found: 312.9.

Provenance & Evidence