Boron tribromide → 4-Chloro-1-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-ol

HRID 913586Notes

Reaction equation

HRID 913586 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[N:7]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:20]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([F:14])([F:12])[F:13])[N:7]([CH2:15][C:16]([F:17])([F:18])[F:19])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 578001464-Chloro-5-(methyloxy)-1-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 578003524-Chloro-1-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-olYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A CH2Cl2 (15 mL) solution of 4-chloro-5-(methyloxy)-1-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1H-benzimidazole (0.14 g, 0.422 mmol) at rt was treated dropwise with BBr3 (1M CH2Cl2, 1.055 ml, 1.055 mmol) and stirred for 2 h. The mixture was quenched with saturated aqueous NaHCO3, adjusted to a pH of 7, and extracted with CH2Cl2. The combined organic portions were washed combined with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification (SiO2; EtOAc/hexanes) afforded the title compound (0.103 g): MS (ESI) m/z 319 (M+1).

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2
  3. washThe combined organic portions were washed
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification (SiO2; EtOAc/hexanes)

Sources & evidence

ORD record
ord-5d0fd9b2033042dcb0eb7a584107d385
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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