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

HRID 1188513노트

반응식

HRID 1188513 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-634113bf61944f7b93073b13a4035f43
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673948B2

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