Pyridiniumtribromide → 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (3.52 g, 17.2 mmol, 1.0 equiv.) was dissolved in chloroform (172 ml) and treated with pyridinium tribromide (5.51 g, 17.2 mmol, 1.0 equiv.). The mixture was stirred at room temperature until LCMS showed almost only product. The solid was collected on top of filter and washed with hexanes. The solid was dissolved in Et2O/EtOAc and neutralized with saturated aqueous sodium bicarbonate. The organic layers were separated, dried with magnesium sulfate, filtered and concentrated in vacuo to provide 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.