Cl[N:2]1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([F:20])[C:11]=1[CH:12]=[N:13][OH:14].[NH4+].[OH-].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[Br:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([F:20])[C:11]=1[C:12]([NH:13][OH:14])=[NH:2]A solution of N-chlorosuccinimide (8.34 g, 62.49 mmol) in DMF (25 ml) was added slowly to a solution of 2-bromo-4-chloro-6-fluoro-benzaldehyde oxime (15 g, 59.52 mmol) in DMF (50 ml) at 50° C. After completion of the addition, the reaction mixture was allowed to stir for 30 min at 50° C. The reaction mixture was then cooled to 3-5° C. and NH4OH (4.6 ml, 119 mmol) was added dropwise. During addition the temperature was maintained between 0-10° C. and the reaction mixture was stirred for another 15 minutes at the same temperature. EtOAc and brine were then added and the mixture was agitated vigorously for 10 minutes before the phases were allowed to settle. The aqueous layer was separated and extracted two times with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated to obtain the title compound as off white solid (13 g, 82%).
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