Azobisisobutyronitrile → 6-Bromo-2-(bromomethyl)quinoline

Reaktionsgleichung

CC(N=NC(C#N)(C)C)(C#N)C.[Br:13]N1C(=O)CCC1=O.[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[C:27]([CH3:32])[CH:26]=[CH:25]2>C(Cl)(Cl)(Cl)Cl>[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[C:27]([CH2:32][Br:13])[CH:26]=[CH:25]2

Komponenten

Versuchsvorschrift

148 mg (1.00 mmol) α,α-azoisobutyronitrile and 8.01 g (45.0 mmol) N-bromosuccinimide are added successively to a solution of 10.0 g (45.0 mmol) 6-bromo-2-methyl-quinoline in 60 mL carbon tetrachloride. The reaction mixture is refluxed for 8 h. It is filtered and the filtrate is washed twice with water. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (PE/EtOAc 4:1).