[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])O.[Na+].[Cl:15][C:16]1[C:24]([C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>O1CCCC1>[Cl:15][C:16]1[C:24]([C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8])=[O:19]A two-layer mixture of a solution of 3-amino-4-fluorophenol (9.00 g, 70.8 mmol) in tetrahydrofuran (50 mL) and aqueous sodium hydrogen carbonate (13.9 g, 166 mmol) solution (100 mL) was vigorously stirred, while adding dropwise a solution of 2-chloro-3-(1-cyanocyclopropyl)benzoyl chloride synthesized above in tetrahydrofuran (60 mL). The reaction mixture was stirred at room temperature for 1 hr. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate (120 mL/40 mL) to give the title compound (23.4 g, 100%) as a brown powder.
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