Reaktion #2851

Reaktionsgleichung

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

N-bromosuccinimide

benzoyl peroxide

→

title compound

Ausbeute 56.9%

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

Ausbeute 56.9%

Lösungsmittel

CCl4

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution is heated
2. 2
   Temperaturto reflux for 16 h
3. 3
   TemperaturThe solution is cooled to ambient temperatures
4. 4
   WaschenThe solution is washed with 1N NaOH and saturated NaCl
5. 5
   TrocknenThe organic layer is dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude material is purified by column chromatography
9. 9
   Wascheneluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Vorschrift

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.

Quelle