Hydrochloric Acid → 1-(2-Chloroethyl)-4-fluorobenzene

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A mixture of 7 g of 2-(4-fluoro-phenyl)-ethanol, 25 mL of chlorobenzene, 42 mL of 37% HCl, and 0.9 g of Aliquat® 336 (tricaprylylmethyl ammonium chloride) was heated to reflux for 3 days, cooled and extracted into 3×100 mL of hexane. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was a crude product of 1-(2-chloro-ethyl)-4-fluoro-benzene:

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