Reaktion #977419

Reaktionsgleichung

2-bromonitrobenzene

isopropenylmagnesium bromide

NH4Cl

→

expected compound

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe medium is left
2. 2
   ExtraktionExtraction
3. 3
   Sonstigethe extract is evaporated
4. 4
   WaschenWashing
5. 5
   SonstigeThe organic layer is dried
6. 6
   Sonstigeevaporated
7. 7
   Sonstigethe residue is chromatographed on silica
8. 8
   Waschenwhile eluting with an AcOEt/cyclohexane (1/9, v/v) mixture

Vorschrift

27.0 g of 2-bromonitrobenzene are placed in 400 ml of THF. The medium is placed under nitrogen and is cooled to −55° C. and then 800 ml of 0.5M isopropenylmagnesium bromide in THF are added dropwise. The medium is left stirring for 1 hour and then it is poured into a saturated NH4Cl solution. Extraction is carried out with ether, the extract is evaporated and then the residue is taken up in DCM. Washing is carried out with a saturated NaCl solution. The organic layer is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (1/9, v/v) mixture. 10.7 g of the expected compound are obtained.

Quelle