Thionyl Chloride → 3,3'-(Chloromethylene)dipyridine

Participants

Reaction Steps

A round bottom flask was charged with di(pyridin-3-yl)methanol (600 mg, 3.22 mmol) and CH2Cl2 (50 mL). Thionyl chloride (353 μl, 4.83 mmol) was added and the reaction was stirred for 18 h at room temperature. The solution was concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 5% 2M NH3 in MeOH) and yielded 3,3′-(chloromethylene)dipyridine (415 mg, 64%). 1H NMR 400 MHz (CDCl3) δ 8.66 (d, J=2.4 Hz, 2H), 8.59 (dd, J=4.7, 1.6 Hz, 2H), 7.76 (m, 2H), 7.34 (m, 2H), 6.17 (s, 1H).

Provenance & Evidence