Thionyl Chloride → 2-Bromo-6-[chloro(4-fluorophenyl)methyl]pyridine

Participants

Reaction Steps

To a mixture of (6-bromopyridin-2-yl)(4-fluorophenyl)methanol in CH2Cl2 (120 mL) @ 0° C. was added SOCl2 (5.870 g, 49.34 mmol). The mixture was allowed to slowly warm to rt and stirred for 16 hr. The mixture was cooled back to 0° C. and quenched with saturated aqueous NaHCO3. The resulting mixture was extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (20-30% CH2Cl2 in Hexanes) to give 2-bromo-6-[chloro(4-fluorophenyl)methyl]pyridine. 1H NMR (500 MHz, CDCl3) δ 7.58 (t, 1H, J=7.7), 7.51 (d, 1H, J=7.6), 7.47-7.39 (m, 3H), 7.04 (t, 2H, J=8.7), 6.08 (s, 1H), LRMS m/z (M+H) Calcd.: 300.0, found: 300.0.

Provenance & Evidence