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

HRID 454181ノート

反応式

HRID 454181 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c6a16ab737e4468b944ce467d07b7152
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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