[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6]C(=O)C)=[C:4]([F:12])[CH:3]=1.Cl>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1A mixture of 119 parts of 4'-chloro-2'-fluoroacetanilide in 475 parts of ethanol and 200 parts of 37% hydrochloric acid was refluxed for 17 hours and the solvent removed at a reduced pressure of 300 mm.Hg to yield the moist, solid hydrochloride salt of 4-chloro-2-fluoroaniline.
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