Thionyl Chloride → 3-(4-Fluorophenyl)propionyl chloride

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A mixture of 3-(4-fluorophenyl)propionic acid (275.1 g, 1.6 mol) and thionyl chloride (300 mL, 4.1 mol) was heated to reflux for 3 h, cooled to room temperature and distilled under aspirator vacuum to give 287.6 g (96%) of 3-(4-fluorophenyl)propionyl chloride as a pale pink oil, b.p., 120°-122° C./15 mm Hg; IR (neat) 1793,1511 cm-1 ; NMR (DMSO-d6): d7.04-7.32 (m, 4H, Ar), 2.50-2.89 (m, 4H, 2XCH2).

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