Boron tribromide → 2-chloro-1H-benzo[d]imidazol-5-ol

HRID 454181노트

반응식

HRID 454181 반응식
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:5]=2[N:6]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 5191972-Chloro-5-methoxy-1H-benzimidazole

생성물 1

HCID 220309582-chloro-1H-benzo[d]imidazol-5-ol수율 159.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Chloro-5-methoxybenzimidazole (0.3 g, 1.64 mmol) was suspended in dichloromethane (20 ml) under argon followed by the addition of boron tribromide (233 ul, 2.46 mmol). The reaction mixture was stirred for 2 hours at ambient temperature. The solvent was evaporated and the resulting powder was added in portions to methanol (30 ml). Silica was added and the solvent was evaporated. The resulting powder was placed on the top of a silica column and the product was eluted off using dichloromethane/methanol (95/5). Evaporation of the solvent and trituration in ether gave 2-chloro-5-hydroxybenzimidazole (440 mg, 99%).

후처리

  1. customThe solvent was evaporated
  2. additionthe resulting powder was added in portions to methanol (30 ml)
  3. additionSilica was added
  4. customthe solvent was evaporated
  5. washthe product was eluted off
  6. customEvaporation of the solvent and trituration in ether

출처 및 근거

ORD 기록
ord-c6a16ab737e4468b944ce467d07b7152
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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