Reaktion #809580

Reaktionsgleichung

2-chloronitrobenzene

isopropenylmagnesium bromide

NH4Cl

→

2-Methyl-7-chloro-1H-indole

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous phase is extracted twice with ether
2. 2
   SonstigeThe organic phase is dried
3. 3
   Sonstigeevaporated
4. 4
   Sonstigethe residue is chromatographed on silica
5. 5
   Wascheneluting with toluene

Vorschrift

Under a nitrogen atmosphere 42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF. The mixture is cooled to −40° C. and then 1.6 1 of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. After 1 hour at −40° C. with stirring the mixture is hydrolyzed with 400 ml of saturated NH4Cl solution. The aqueous phase is extracted twice with ether. The organic phase is dried and then evaporated and the residue is chromatographed on silica, eluting with toluene. This gives 20.3 g of the expected compound.

Quelle