Boron tribromide → 2-(Trifluoromethyl)-1h-indol-5-ol

HRID 454049ノート

反応式

HRID 454049 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6]2.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([F:15])([F:13])[F:14])=[CH:6]2

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 153353435-Methoxy-2-(trifluoromethyl)-1H-indole

生成物 1

HCID 220307102-(Trifluoromethyl)-1h-indol-5-ol収率 39%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5-methoxy-2-trifluoromethylindole (800 mg, 3.7 mmol) in methylene chloride (6 ml) was cooled to −15° C. and a solution of 1M boron tribromide in methylene chloride (7.44 ml, 7.4 mmol) was added in portions. The mixture was allowed to warm to ambient temperature and was stirred for 45 minutes. After cooling to 0° C., saturated aqueous sodium hydrogen carbonate (25 ml) was added. The mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether. After removal of the volatiles by evaporation, the solid was triturated with pentane, collected by filtration and dried under vacuum to give 5-hydroxy-2-trifluoromethylindole (290 mg, 39%).

後処理

  1. temperatureAfter cooling to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe volatiles were removed by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with ethyl acetate/petroleum ether
  7. customAfter removal of the volatiles
  8. customby evaporation
  9. customthe solid was triturated with pentane
  10. filtrationcollected by filtration
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-be2817894e5f44cbbf5d3089e4f07c91
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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