Thionyl Chloride → 8-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline

Participants

Reaction Steps

Prepared according to Procedure C using (2-(2-chlorophenyl)-8-chloroquinolin-3-yl)methanol (0.675 g, 2.22 mmol) and SOCl2 (0.81 mL). 8-Chloro-3-(chloro-methyl)-2-(2-chlorophenyl)quinoline was obtained as a yellow foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (1 H, s), 7.88 (1 H, dd, J=8.2, 1.2 Hz), 7.81 (1 H, dd, J=7.4, 1.2 Hz), 7.48 (1 H, d, J=7.4 Hz), 7.42-7.46 (1 H, m), 7.27-7.41 (3 H, m), 4.63 (1 H, d, J=9.8 Hz), 4.33-4.45 (1 H, m) Mass Spectrum (ESI) m/e=322.0 and 324.0 (M+1)

Provenance & Evidence