Reaktion #51211

Reaktionsgleichung

anisidine

N,N-dimethylaniline

2-bromo-4-methoxyacetophenone

→

indole

2-Phenyl Indole

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Sonstigea dark colored solid was formed
3. 3
   ExtraktionThe aqueous layer was extracted with EtOAc several times
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeSolvent was removed under the reduced pressure
7. 7
   Sonstigeto afford a dark brown colored solid
8. 8
   SonstigePurification
9. 9
   Sonstigeby recrystallization in EtOH

Vorschrift

To a boiling mixture of in-anisidine (1.56 ml, 20.0 minol) and N,N-dimethylaniline (3.5 ml) was added 2-bromo-4-methoxyacetophenone (1.37 g in EtOAc, 6.00 mmol) slowly by syringe. After addition, the mixture was kept at 170° C. for 1 hour. The reaction mixture was cooled to room temperature and a dark colored solid was formed. EtOAc was added along with HCI (2 N). The aqueous layer was extracted with EtOAc several times. The combined organic layers were washed with brine, and dried over MgSO4. Solvent was removed under the reduced pressure to afford a dark brown colored solid. Purification by recrystallization in EtOH afforded indole 31 as a white crystallinc material.

Quelle