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

HRID 2102019ノート

反応式

HRID 2102019 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cc877519194149b0bb09646b468a4cba
出典データセット
uspto-grants-2009_08
特許番号
US07572820B2

反応ノート

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