Reacción #2851

Ecuación de reacción

4-(benzhydrylidene-amino)-3-methyl-benzonitrile

N-bromosuccinimide

benzoyl peroxide

→

title compound

Rendimiento 56.9%

4-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrile

Rendimiento 56.9%

Disolventes

CCl4

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution is heated
2. 2
   Temperaturato reflux for 16 h
3. 3
   TemperaturaThe solution is cooled to ambient temperatures
4. 4
   LavadoThe solution is washed with 1N NaOH and saturated NaCl
5. 5
   SecadoThe organic layer is dried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude material is purified by column chromatography
9. 9
   Lavadoeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Procedimiento

To a solution of 4-(benzhydrylidene-amino)-3-methyl-benzonitrile (1.36 g, 4.27 mmol) in 40 mL of CCl4 is added N-bromosuccinimide (0.84 g, 4.7 mmol) and benzoyl peroxide (0.22 g, 0.64 mmol). The solution is heated to reflux for 16 h. The solution is cooled to ambient temperatures. The solution is diluted with CH2Cl2. The solution is washed with 1N NaOH and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (0.91 g, 2.43 mmol) is obtained as an oil.

Fuente