Reaktion #5957

Reaktionsgleichung

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

phthalimide

potassium carbonate

→

title compound

Ausbeute 71.0%

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

Ausbeute 71.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturat reflux for 24 hours
3. 3
   FiltrationAt that time the mixture is filtered through celite
4. 4
   SonstigeThe residue is crystallized from ethyl acetate

Vorschrift

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.

Quelle