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

HRID 2423545Notes

Reaction equation

HRID 2423545 reaction equation
[Br:1]Br.[CH3:3][C:4]([CH3:17])([CH3:16])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[CH3:18][C:19]([CH3:32])([CH3:31])[CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=2[N:23]=[N:22]1>C(O)(=O)C>[Br:1][C:11]1[C:10]2[N:6]([CH2:5][C:4]([CH3:17])([CH3:16])[CH3:3])[N:7]=[N:8][C:9]=2[CH:14]=[CH:13][C:12]=1[OH:15].[Br:1][C:29]1[C:24]2[N:23]=[N:22][N:21]([CH2:20][C:19]([CH3:32])([CH3:31])[CH3:18])[C:25]=2[CH:26]=[CH:27][C:28]=1[OH:30]

Participants

6

Reactant 3

HCID 24408BromineHCID 574249931-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-olHCID 1361165381-(2,2-Dimethylpropyl)-1h-1,2,3-benzotriazol-6-ol

Product 2

HCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-olHCID 1361165397-Bromo-1-(2,2-dimethylpropyl)-1h-1,2,3-benzotriazol-6-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. customprepared as a 1.3:1.0 mixture
  2. concentrationthe reaction was concentrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-bf0c3fa440a54a72941fe65cf313624b
Source dataset
uspto-grants-2011_06
Patent number
US07960417B2

Reaction notes

Loading…