Reaktion #809581

Reaktionsgleichung

2-bromonitrobenzene

isopropenylmagnesium bromide

NH4Cl

→

7-Bromo-2-methyl-1H-indole

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe mixture is left
2. 2
   ExtraktionIt is extracted with ether
3. 3
   Sonstigethe extract is evaporated
4. 4
   WaschenIt is washed with saturated NaCl solution
5. 5
   SonstigeIt is dried
6. 6
   Sonstigeevaporated
7. 7
   Sonstigethe residue is chromatographed on silica
8. 8
   Wascheneluting with an AcOEt/cyclohexane (1/9; v/v) mixture

Vorschrift

27.0 g of 2-bromonitrobenzene are placed in 400 ml of THF. The mixture is placed under nitrogen and cooled to −55° C. and then 800 ml of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. The mixture is left with stirring for 1 hour and then poured into saturated NH4Cl solution. It is extracted with ether, the extract is evaporated and then the residue is taken up in DCM. It is washed with saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica, eluting with an AcOEt/cyclohexane (1/9; v/v) mixture. This gives 10.7 g of the expected compound.

Quelle