Reaktion #77773

Reaktionsgleichung

5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

K2CO3

1,4-dibromobutane

→

5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Ausbeute 49.4%

Lösungsmittel

ether

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   ExtraktionThe aqueous phase was extracted with ether
3. 3
   Waschenthe organic phases were washed with water
4. 4
   Trocknendried over Na2SO4

Vorschrift

290 mg (1 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 5 ml acetone were treated with 320 mg (3 mmol) K2CO3 (powdered) and 0.23 ml (2 mmol) 1,4-dibromobutane. The suspension was stirred at 50° C. for 4 h, cooled to RT, and was diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 210 mg (49%) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as colorless solid, MS: 423 (M, 1Br, 1Cl).

Quelle