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

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To (4-cyclopentyl-3-(trifluoromethyl)phenyl)methanol (110 g, 113 mmol), thionyl chloride (329 mL, 4.50 mol) was added dropwise at such a rate as to maintain the internal temperature between 10-25° C. (cooled with ice-water). The resulting mixture was stirred at 50° C. for 3.5 h followed by 6 h at 25° C. The mixture was concentrated under reduced pressure and the resulting oily residue poured into ice-water (450 mL) under vigorous stirring. The layers were separated and the aqueous phase extracted with CH2Cl2 (3×400 mL). The combined organic layers were washed with saturated NaHCO3 (400 mL), brine (2×400 mL), dried (Na2SO4), filtered over fresh Na2SO4, and concentrated in vacuo to give the title compound as a pale yellow oil (113.3 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.67-1.57 (m, 2H), 1.81-1.71 (m, 2H), 1.94-1.84 (m, 2H), 2.16-2.07 (m, 2H), 3.39 (quintet, J=8.6 Hz, 1H), 4.61 (s, 2H), 7.49 (d, J=8.4 Hz, 1H), 7.54 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.63 (d, J=1.6 Hz, 1H).

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