[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].COC(=O)[C:21](Cl)([F:23])[F:22].O>CN(C)C=O>[F:22][CH:21]([F:23])[O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]5-fluoro-2-nitrophenol (3.1 g) was dissolved in dimethylformamide (40 mL), and potassium carbonate (4.2 g) and chlorodifluoroacetic acid methyl ester (3.2 mL) were slowly dropwisely added at room temperature. The mixed solution was isothermally maintained to 100° C., stirred for 2 hours, and then cooled to room temperature. Then, the resultant was added with water (100 ml) and extracted with diethyl ether (200 mL). The resulting organic layer was washed with saturated brine and dried with sodium sulfate and filtered. The resulting mixture was purified by column chromatography (silica gel, hexane/ethyl acetate) to obtain a target compound as a bright yellow solid.
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