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

HRID 1626959Notes

Reaction equation

HRID 1626959 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>C(Cl)Cl>[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

4

Reactant 2

HCID 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 (Example 1-1) (8.97 g, 30.1 mmol, 1.0 equiv.) in DCM (150 ml) at 0° C., was added slowly 1 M solution of BBr3 (60.2 ml, 60.2 mmol, 2.0 equiv.) in DCM. The reaction mixture was allowed to warm up to room temperature overnight. LCMS showed completion. The reaction mixture was quenched with water, neutralized to pH=7, then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to give 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (Example 1-2). 1H NMR (500 MHz, CDCl3) δ 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. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-45ccc56726cd40eaafa5bc758dc2b106
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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