FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22](C)(C)[CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].S(=O)(=O)(O)O.C(O)C>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16]
Trifluoroacetic acid (25 ml) was added to a solution of di-tert-butyl (3-fluoro-4-nitrophenyl)malonate (5.11 g, 14.4 mmol) in methylene chloride (50 ml). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to yield a colorless solid substance. To the solid substance were added concentrated sulfuric acid (1 ml) and ethanol (50 ml) and the mixture was heated and refluxed for 2 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Ice water (100 ml) was poured in the residue, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby ethyl 3-fluoro-4-nitrophenylacetate (3.15 g, 96%) was obtained as a yellow oil.
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