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

HRID 1626963Notes

Reaction equation

HRID 1626963 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH: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[OH:13]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 574249931-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

Product 1

HCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (10) (3 mg, 0.015 mmol, 1.0 equiv.) in CHCl3 (500 μL), was added slowly pyridinium tribromide (4.67 mg, 0.015 mmol, 1.0 equiv.). The reaction mixture was stirred at room temperature until LCMS showed mostly the desired product. The reaction mixture was quenched with water, neutralized to pH=7, then extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to give 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (Example 1-2). LRMS m/z (M+H) 283.9 and 285.9 (intensity ratio ˜1:1) found, 284.0 and 286.0 required.

Sources & evidence

ORD record
ord-29ac50966bde4ff9b094e3a6b1784caa
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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