Reaktion #809582

Reaktionsgleichung

isopropenylmagnesium bromide

2,3-dichloronitrobenzene

NH4Cl

→

6,7-Dichloro-2-methyl-1H-indole

Lösungsmittel

Et2O

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture is left
2. 2
   Waschenthe aqueous phase is washed twice with Et2O
3. 3
   Einengenconcentrated to dryness
4. 4
   ExtraktionThe product is extracted with DCM
5. 5
   Waschenwashed twice with water
6. 6
   SonstigeIt is dried
7. 7
   Sonstigeevaporated
8. 8
   Sonstigethe residue is chromatographed on a hexane/AcOEt (95/5; v/v) mixture

Vorschrift

1600 ml of isopropenylmagnesium bromide at 0.5 M in THF are introduced under nitrogen and cooled to −20° C., 51.2 g of 2,3-dichloronitrobenzene in 250 ml of anhydrous THF are added and then the mixture is left with stirring at −20° C. for 1 hour. The reaction mixture is poured at −20° C. into 1 liter of saturated NH4Cl solution and diluted with Et2O and then the aqueous phase is washed twice with Et2O. The organic phases are combined and concentrated to dryness. The product is extracted with DCM and washed twice with water and then with saturated NaCl solution. It is dried and then evaporated and the residue is chromatographed on a hexane/AcOEt (95/5; v/v) mixture. This gives 24.27 g of the expected compound, m.p.=70–71° C.

Quelle