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

HRID 1633613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633613
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fd7faa6e24e940f88ed73fa8112c5f67
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

Notizen zur Reaktion

Wird geladen…