Pyridiniumtribromide → 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine
Reaktionsgleichung
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[N:5]1.[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:16][C:12]1[C:7]2[N:6]=[N:5][N:4]([CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])[C:8]=2[CH:9]=[CH:10][C:11]=1[NH2:13]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
1-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (3.52 g, 17.23 mmol, 1.0 equiv.) was dissolved in chloroform (172 ml) and treated with pyridinium tribromide (5.51 g, 17.23 mmol, 1.0 equiv.). The mixture was stirred at room temperature until LCMS showed almost only product was observed. The mixture was filtered and the solid was washed with hexane, which was dissolved in diethyl ether/ethyl acetate and neutralized with saturated aqueous sodium bicarbonate. The organic extracts were dried with magnesium sulfate, filtered and concentrated in vacuo, providing the titled compound as a pale white solid. 1H NMR (500 MHz, CD3OD) 7.30 (d, 1H, J=8.8 Hz), 7.07 (sb, 3H), 7.02 (d, 1H, J=8.8 Hz), 4.34 (s, 2H), 1.03 (s, 9H) ppm. LRMS m/z (M+H) 283.0 and 285.0 (intensity ratio ˜1:1) found, 283.1 and 285.1 required.