[C-]#N.[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1.[CH3:19][NH:20]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:19]#[N:20])=[CH:6][CH:7]=1)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1An oven dried screw cap test tube was charged with NaCN (91 mg, 1.857 mmol), dried KI (51 mg, 0.307 mmol, 20 mol %), CuI (30 mg, 0.157 mmol, 10 mol %), (4-bromophenyl)-phenyl-methanone (404 mg, 1.548 mmol), evacuated and backfilled with argon three times. N,N′-dimethylethylenediamine (165 μL, 1.550 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed complete conversion of starting material with formation of title product (confirmed by GC-MS).
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