N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:10]=1N.[ClH:21]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:10]=1[Cl:21]To anhydrous copper(II)chloride (6.3 g, 47 mmol) in acetonitrile (100 mL) was added tert-butyl nitrite (6.85 mL, 58 mmol), followed dropwise by a solution of 2-bromo-4-(trifluoromethoxy)aniline (10 g, 39 mmol) in acetonitrile (15 mL). The solution was stirred at ambient temperature for 1 hour then poured into hydrochloric acid (250 mL, 2M). The suspension formed was extracted with diethyl ether (2×250 mL) and the extracts were dried (MgSO4). Concentration yielded the title compound as an oil (7.82 g, 28 mmol).
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