[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9]([F:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[N:16]1([O-])C2C=CC=CC=2N=N1.[NH4+].Cl.CN(C)CCCN=C=NCC.C(N1CCOCC1)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9]([F:15])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:16])=[O:5]2-Chloro-4-fluoro-3-(trifluoromethyl)benzoic acid (0.560 g, 2.31 mmol), ammonium 1H-1,2,3-benzotriazol-1-olate (0.534 g, 3.47 mmol, prepared as described below), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.643 g, 3.47 mmol), and N-ethyl morpholine (0.594 ml, 4.62 mmol) were stirred together in dichloromethane (30 ml) for a total of 3 hrs. Saturated aqueous sodium hydrogen carbonate (30 ml) was added and the mixture was stirred for 15 minutes. The organic layer was separated using a hydrophobic frit and then washed with 2N aqueous hydrogen chloride (2×50 ml). Separation of the organic layer, again using a hydrophobic frit, and evaporation in vacuo gave 2-chloro-4-fluoro-3-(trifluoromethyl)benzamide (0.493 g) as an off-white solid which was used without further purification in the subsequent step.
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