Bromine → 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

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Reaction Steps

Bromine (60 μL, 1.2 mmol) was added to a solution of 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-6-ol & 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (0.22 g, 1.1 mmol), prepared as a 1.3:1.0 mixture according to example 6, and acetic acid (10 mL) at rt. After 1 h, the reaction was concentrated and purified by silica gel chromatography to give 7-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-6-ol and 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol. MS (ESI): 284/286 (M+H). Similar procedures as outlined in example 1 were followed using 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol. 1H NMR (500 MHz, DMSO) δ 7.96 (d, 2H), 7.92 (d, 1H), 7.52 (d, 1H), 7.16 (d, 2H), 4.50 (s, 2H), 4.26 (t, 2H), 4.18 (t, 2H), 2.02-1.91 (m, 4H), 0.96 (s, 9H). MS (ESI): 500/502 (M+H).

Provenance & Evidence