Thionyl Chloride → 5-Chloro-3-(chloromethyl)-2-(2-(trifluoromethyl)phenyl)quinoline hydrochloride

Participants

Reaction Steps

A solution of (5-chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol (2.180 g, 6.455 mmol) in 22 mL of CHCl3 was treated with thionyl chloride (2.348 mL, 32.27 mmol) dropwise, and the reaction mixture was stirred at room temperature. After 1.5 hr, the mixture was concentrated under reduced pressure and co-evaporated three times with CH2Cl2 to give 5-chloro-3-(chloromethyl)-2-(2-(trifluoromethyl)phenyl)quinoline hydrochloride as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.86 (1 H, d, J=0.6 Hz), 7.99-8.05 (1 H, m), 7.94 (1 H, dd, J=7.4, 1.0 Hz), 7.88-7.92 (1 H, m), 7.81-7.87 (2 H, m), 7.74-7.81 (1H, m), 7.61-7.66 (1 H, m), 4.77 (2 H, d, J=79.0 Hz); LC-MS (ESI) m/z 356.0 and 358.0 [M+H]+ (Exact Mass of neutral form: 355.014). The yellow solid was carried on crude without purification for the next step.

Provenance & Evidence