[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1.[C:13](Cl)(Cl)=[S:14].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.CCCCCCC>[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([N:6]=[C:13]=[S:14])=[C:4]([F:12])[CH:3]=1To a cold (0° C.), stirring mixture of 12.0 g (0.0630 mole) of 4-chloro-2-fluoro-5-nitroaniline in 100 mL of methylene chloride was added dropwise 7.3 g (0.063 mole) of thiophosgene. While maintaining a temperature of 0° C., 13.2 g (0.130 mole) of triethylamine was added dropwise to the mixture. After complete addition, the mixture was allowed to warm to room temperature and stir for approximately 18 hours. The solvent was evaporated under reduced pressure leaving a residue. This residue was stirred in a mixture of ethyl acetate and n-heptane (30:70). The insoluble amine hydrochloride salts were removed by filtration. The filtrate was evaporated under reduced pressure to yield 14.0 g of 4-chloro-2-fluoro-5-nitrophenylisothiocyanate.
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