Hydrochloric Acid → 5-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole

HRID 1633613ノート

反応式

HRID 1633613 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.[OH-].[K+].Cl>O.CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 99931-Bromo-4-fluorobenzeneHCID 146245-BenzyloxyindoleHCID 14797Potassium Hydroxide

生成物 1

HCID 111979085-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To 22.3 g (0.1 mol) 5-benzyloxyindole in 110 ml (1.0 mol) 1-bromo-4-fluorobenzene were added 28 g (0.5 mol) powdered potassium hydroxide and 6.4 g (0.1 mol) Cu as powder. The suspension was heated to reflux for 2 h. At RT, ether and water were added, the mixture was acidified with 2M HCl and extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with a gradient hexane-hexane/EtOAc 19:1-9:1 yielded 19 g (60%) 5-Benzyloxy-1-(4-fluoro-phenyl)-1H-indole as colorless solid, MS: 318 (MH+).

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 2 h
  3. extractionextracted with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-fd7faa6e24e940f88ed73fa8112c5f67
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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