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

HRID 872267Notes

Reaction equation

HRID 872267 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16]C.B(Br)(Br)Br.O>ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:14])([CH3:13])[CH3:15])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 676081624-bromo-1-(2,2-dimethylpropyl)-5-methoxy-1H-1,2,3-benzotriazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-1-(2,2-dimethylpropyl)-5-methoxy-1H-1,2,3-benzotriazole (1-5) (8.97 g, 30.1 mmol, 1.0 equiv.) in dichloromethane (150 ml) at 0° C., was added slowly a 1M solution of BBr3 (60.2 ml, 60.2 mmol, 2.0 equiv.) in dichloromethane. The reaction mixture was allowed to warm up to room temperature and was stirred for an additional 14 hours. LCMS showed completion. The reaction mixture was treated with water, neutralized to pH=7, then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to give provide 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (1-6). 1H NMR (500 MHz, CDCl3) 7.36 (d, 1H, J=9.0 Hz), 7.24 (d, 1H, J=9.0 Hz), 4.37 (s, 2H), 1.04 (s, 9H) ppm. LRMS m/z (M+H) 283.9 and 285.9 (intensity ratio ˜1:1) found, 284.0 and 286.0 required.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give

Sources & evidence

ORD record
ord-51e54d33e1a741d78dc0c5e0df760820
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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