Boron tribromide → 6-Bromo-1H-indazol-5-ol

HRID 2195486ノート

反応式

HRID 2195486 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 569716546-Bromo-5-methoxy-1H-indazole

生成物 1

HCID 591599466-Bromo-1H-indazol-5-ol収率 75.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 6-bromo-5-methoxy-1H-indazole (60 g, 0.265 mol) in DCM (1300 mL) is added a solution of BBr3 (105 g, 0.42 mol) in DCM (200 mL) at 0° C. The reaction mixture is warmed to RT and stirred overnight. Then the reaction solution is quenched with MeOH at 0° C. The solvent is removed in vacuo and the residue is neutralized with NaHCO3 solid. The mixture is partitioned by water (1500 mL) and EtOAc (1500 mL). The aqueous layer is extracted with EtOAc (1500 mL) two times. The combined organic layers are dried and concentrated to give crude product, which is purified by silica gel column chromatography (PE:THF=2:1) to give the desired product (42.5 g, 75% yield). MS (m/z): 215.0 (M+H).

後処理

  1. customThen the reaction solution is quenched with MeOH at 0° C
  2. customThe solvent is removed in vacuo
  3. customThe mixture is partitioned by water (1500 mL) and EtOAc (1500 mL)
  4. extractionThe aqueous layer is extracted with EtOAc (1500 mL) two times
  5. customThe combined organic layers are dried
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customis purified by silica gel column chromatography (PE:THF=2:1)

出典と根拠

ORDレコード
ord-7a5e0171ce8d49e5bc8197fe01ba92d7
出典データセット
uspto-grants-2012_12
特許番号
USRE043878E1

反応ノート

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