Thionyl Chloride → 3-(4-Trifluoromethylphenyl)-benzyl chloride

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Reaction Steps

The alcohol 2.2 (15 g, 59.5 mmol) was dissolved in anhydrous dichloromethane (100 mL). Thionyl chloride (10 mL) was slowly added dropwise to the above solution. The resulting mixture was stirred at room temperature for 24 hours. The organic solvent was removed under vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 20% DCM in hexanes). Fractions containing the desired product 2.3 were combined and concentrated to a white solid (14.0 g). 1H NMR (400 MHz) (CDCl3) δ 7.73 (4H, s); 7.65 (1H, s); 7.58 (1H, s); 7.52-7.28 (2H, m); 4.69 (2H, s).

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