Реакция #2851

Уравнение реакции

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

N-bromosuccinimide

benzoyl peroxide

→

title compound

Выход 56.9%

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

Выход 56.9%

Растворители

CCl4

CH2Cl2

Условия реакции

Обработка

1. 1
   ТемператураThe solution is heated
2. 2
   Температураto reflux for 16 h
3. 3
   ТемператураThe solution is cooled to ambient temperatures
4. 4
   ПромывкаThe solution is washed with 1N NaOH and saturated NaCl
5. 5
   СушкаThe organic layer is dried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe crude material is purified by column chromatography
9. 9
   Промывкаeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

Методика

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.

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