[N+](C1C=CC=C2C(NC(=O)C=12)=O)([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1.[Br:31]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>CN(C=O)C.C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1
9.79 g (50.93 mmol) of 3-nitrophthalimide are dissolved in 450 ml of DMF, and 10.56 g (76.39 mmol) of potassium carbonate are added. The suspension is treated with ultrasound for 10 min. 10.7 g (50.93 mmol) of 2-[4-(bromomethyl)phenyl]acetonitrile (obtained by reaction of 2-(4-methylphenyl)acetonitrile with N-bromosuccinimide (NBS) and azobisisobutyronitrile (AIBN) in carbon tetrachloride, cf. E. Laurent, B. Marquet, R. Tardivel; Tetrahedron; 47; 24; 1991; pp. 3969-3980) are then added, and the reaction mixture is stirred at room temperature for 20 h. The suspension is then poured into a mixture of 300 ml of 2 N hydrochloric acid and 3 l of water. The crystals formed are filtered off with suction, washed with water and dried under reduced pressure. This gives 12 g (73% of theory) of the desired compound. Rf (SiO2, CH2Cl2/EtOH=100/1)=0.55, MS=322.2 (M+H+).
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