Reaction #2851

Reaction equation

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

N-bromosuccinimide

benzoyl peroxide

→

title compound

Yield 56.9%

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

Yield 56.9%

Solvents

CCl4

CH2Cl2

Conditions

Workup

1. 1
   TemperatureThe solution is heated
2. 2
   Temperatureto reflux for 16 h
3. 3
   TemperatureThe solution is cooled to ambient temperatures
4. 4
   WashThe solution is washed with 1N NaOH and saturated NaCl
5. 5
   DryingThe organic layer is dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe crude material is purified by column chromatography
9. 9
   Washeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Procedure

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.

Source