Reaktion #977416

Reaktionsgleichung

2-chloronitrobenzene

isopropenylmagnesium bromide

NH4Cl

→

expected compound

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
   Waschenwhile eluting with toluene

Vorschrift

42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF under a nitrogen atmosphere. The mixture is cooled to −40° C. and then 1.61 of 0.5M isopropenylmagnesium bromide in THF are added dropwise. After stirring at −40° C. for 1 hour, the mixture is hydrolysed with 400 ml of a 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 while eluting with toluene. 20.3 g of the expected compound are obtained.

Quelle