Water → 1-Benzyl-5-Bromo-1H-Indole

HRID 583601

Reaktionsgleichung

[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[CH2:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

In a suspension of 26.6 g of KOH in 200 ml of dimethylformamide, 20.1 g of solid 5-bromoindole was incorporated while being stirred. The mixture was stirred for 50 minutes at room temperature, and 25.4 g of benzyl chloride was dropwise added to the mixture over a period of 16 minutes at a temperature of not higher than 30° C. The reaction mixture was maintained at 30° C. in an oil bath for 5 hours with stirring. After completion of the reaction, 200 ml of water was added and the thus-formed aqueous phase was extracted with 120 ml of ether three times. The thus-obtained organic phase was washed with water and dried over sodium sulfate overnight. The dried product was concentrated to dryness and then recrystallized from isopropyl ether to give 23.5 g of N-benzyl-5-bromoindole. The yield was 80% by mole.

Aufarbeitung

stirringThe mixture was stirred for 50 minutes at room temperature
stirringwith stirring
additionwas added
extractionthe thus-formed aqueous phase was extracted with 120 ml of ether three times
washThe thus-obtained organic phase was washed with water
dry with materialdried over sodium sulfate overnight
concentrationThe dried product was concentrated to dryness
customrecrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-7b241651f8db4175b431fd2f7a415335
Quelldatensatz: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05929281

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