OS(O)(=O)=O.N([O-])=O.[Na+].N[C:11]1[C:12]([Cl:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[C:14]#[N:15].[BrH:21]>C(O)(=O)C>[Br:21][C:11]1[C:12]([Cl:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[C:14]#[N:15]To 1 mL of conc. H2SO4 was portionwise added sodium nitrite (1.38 mmol). After complete dissolution, a solution of 3-amino-2,6-dichlorobenzonitrile (1.24 mmol) in 2.5 mL glacial acetic acid was added at 0° C. After 30 min at 0° C., a precooled solution of CuBr (2.76 mmol) in 0.5 mL HBr (48% in H2O) was slowly added. The reaction was stirred at 0° C. for 45 min and then at RT for 45 min. The mixture was quenched with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give the desired product as brown solid.
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