Ethanol → Ethyl 3-(2-fluorophenyl)prop-2-enoate

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A solution of 2-fluorocinnamic acid (48.4 g, 0.29 mol, Aldrich) and thionyl chloride (5 mL) in ethanol (650 mL) was heated to reflux for 48 h. The mixture was concentrated in vacuo. The residue was taken up in ethyl acetate, washed successively with a 5% aqueous sodium bicarbonate solution, water and brine, and dried (Na2SO4). Filtration and concentration gave 54.25 g (96%) of crude ethyl 2-fluorocinnamate. This material was used without further purification.

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