Thionyl Chloride → 4-(Chloromethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzene

To a solution of (4-(cyclohexylmethyl)-3-(trifluoromethyl)phenyl)methanol (0.060 g, 0.220 mmol) in toluene (2 mL) was added thionyl chloride (1.32 mmol). The reaction was heated to 75° C. for 3 h and quenched with water at 0° C. The mixture was extracted with hexanes (twice). The combined organics were washed with saturated NaHCO3(aq), dried over MgSO4, and concentrated to give the title compound as an oil (0.220 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-1.06 (m, 2H), 1.12-1.23 (m, 3H), 1.61-1.74 (m, 6H), 2.66 (d, J=6.95 Hz, 2H), 4.59 (s, 2H), 7.30 (d, J=7.96 Hz, 1H), 7.47 (d, J=7.96 Hz, 1H), 7.63 (s, 1H).