Reacción #5957

Ecuación de reacción

Methyl 2-[4-(bromomethylene)phenyl]benzoate

phthalimide

potassium carbonate

→

title compound

Rendimiento 71.0%

N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

Rendimiento 71.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is heated
2. 2
   Temperaturaat reflux for 24 hours
3. 3
   FiltraciónAt that time the mixture is filtered through celite
4. 4
   OtroThe residue is crystallized from ethyl acetate

Procedimiento

Methyl 2-[4-(bromomethylene)phenyl]benzoate (1.22 g, 0.04 mole), phthalimide (0.59 g, 0.04 mole), and potassium carbonate (0.55 g, 0.04 mole) are combined in 120 mL acetonitrile. The mixture is heated at reflux for 24 hours. At that time the mixture is filtered through celite and rotovapped to a residue. The residue is crystallized from ethyl acetate to afford 1.1 g (71%) of the title compound as a tan solid mp 148°-150° C. 1H NMR (CDCl3) 7.9-7.1 (12H, m); 4.92 (2H, s); 3.63 (3H, s). Mass Spec. (DCl) m/z 372 (M+H). Analysis--calc'd for C23H17NO4.1/2 H2O: C, 72.62; H, 4.77: N, 3.68; found: C, 72.88; H, 4.55; N, 3.77.

Fuente