Reaktion #362927

Reaktionsgleichung

sodium hydride

1-bromo-3-chloropropane

1H-indole

1-bromo-3-chloropropane

benzene

→

1-(3-chloropropyl)-1H-indole

Ausbeute 83.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added dropwise, during a period of 30 minutes
2. 2
   Sonstigeat 40° C
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for 1 hour at 50° C
5. 5
   TemperaturAfter cooling
6. 6
   ExtraktionThe product was extracted with benzene
7. 7
   SonstigeThe extract was separated
8. 8
   Sonstigedried
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    workup.DISTILLATIONThe residue was distilled

Vorschrift

To a stirred mixture of 58.5 g of 1H-indole, 107.5 ml of 1-bromo-3-chloropropane, 15 mg of N,N,N-triethylbenzenemethanaminium chloride and 450 ml of benzene were added dropwise, during a period of 30 minutes, 250 ml of a sodium hydride dispersion 60% at 40° C. Upon completion, stirring was continued for 1 hour at 40° C. Another amount of 15 ml of 1-bromo-3-chloropropane was added and stirring was continued for 1 hour at 50° C. After cooling, the reaction mixture was poured into water. The product was extracted with benzene. The extract was separated, dried, filtered and evaporated. The residue was distilled, yielding 80 ml (83%) of 1-(3-chloropropyl)-1H-indole (interm. 10); bp. 120-125° C.

Quelle