Reacción #51683

Ecuación de reacción

water

bromoacetonitrile

5-nitroindole

sodium hydride

→

(5-Nitro-indol-1-yl)-acetonitrile

Rendimiento 97.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added via syringe
2. 2
   OtroAfter 1 h reaction time at the same temperature
3. 3
   OtroThe precipitate, (5-nitro-indol-1-yl)-acetonitrile, was collected (1.96, 97% yield)
4. 4
   Otrowas used without further purification

Procedimiento

To a solution of 5-nitroindole (1.62 g, 10 mmole) in DMF (15 ml) was added sodium hydride (60% in oil, 0.440 g, 11 mmole). The reaction mixture was stirred for 30 minutes at room temperature after which time bromoacetonitrile (1.25 g, 10.5 mmole) was added via syringe. After 1 h reaction time at the same temperature, the mixture was poured into 200 ml of water. The precipitate, (5-nitro-indol-1-yl)-acetonitrile, was collected (1.96, 97% yield) and was used without further purification.

Fuente