Réaction #2851

Équation de réaction

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

N-bromosuccinimide

benzoyl peroxide

→

title compound

Rendement 56.9%

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

Rendement 56.9%

Solvants

CCl4

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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