Reacción #46780

Ecuación de reacción

NH4Cl

isopropenylmagnesium bromide

2-fluoronitrobenzene

→

expected compound

7-Fluoro-2-methyl-1H-indole

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe mixture is left
2. 2
   Extracciónthe aqueous phase is extracted with ether
3. 3
   Concentraciónthe combined organic phases are concentrated under vacuum
4. 4
   Extracciónextracted with DCM
5. 5
   Lavadothe organic phase is washed with water and with a saturated NaCl solution
6. 6
   Secadodried over MgSO4
7. 7
   Otrothe solvent is evaporated under vacuum
8. 8
   OtroThe residue is chromatographed on silica gel, elution

Procedimiento

1600 ml of a 0.5M solution of isopropenylmagnesium bromide in THF are cooled to −25° C. under an argon atmosphere, a solution of 37.65 g of 2-fluoronitrobenzene in 250 ml of THF is then added dropwise and the mixture is left stirring at −20° C. for 1 hour. The reaction mixture is poured into a saturated NH4Cl solution, the aqueous phase is extracted with ether and the combined organic phases are concentrated under vacuum. The residue is taken up in water and extracted with DCM, the organic phase is washed with water and with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a cyclohexane/EtOAc mixture (95/5; v/v). 12.35 g of the expected compound are obtained.

Fuente