[N:1]([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:7]=1[NH2:8].Cl.[CH3:19][O:20][CH2:21][C:22](=[O:28])[CH2:23][C:24]([O:26][CH3:27])=[O:25].C([O-])(=O)C.[Na+]>O.CO>[F:5][C:6]1[CH:12]=[C:11]([O:13][C:14]([F:15])([F:16])[F:17])[CH:10]=[CH:9][C:7]=1[NH:8][N:1]=[C:23]([C:22](=[O:28])[CH2:21][O:20][CH3:19])[C:24]([O:26][CH3:27])=[O:25]A solution of sodium nitrite (1.9 g, 28 mmol) in H2O (10 mL) was added dropwise to a solution of 2-fluoro-4-(trifluoromethoxy)aniline (4.6 g, 24 mmol) in 6 M HCl (24 mL, 144 mmol) at 0° C. After stirring for 15 min at 0° C., the mixture was added to a suspension of methyl 4-methoxyacetoacetate (3.1 mL, 24 mmol) and sodium acetate (12 g, 144 mmol) in MeOH (50 mL) pre-cooled at 0° C. The formed precipitate was collected by filtration, washed with water and dried under reduced pressure to give the title compound (4.8 g, 58% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.51 (3H, s), 3.94 (3H, s), 4.65 (2H, s), 7.06-7.14 (2H, m), 7.59-7.68 (1H, m), 12.98 (1H, brs).
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