Reaktion #49281

Reaktionsgleichung

water

methyl acrylate

triethylamine

methyl acrylate

triethylamine

methyl acrylate

triethylamine

3-Amino-4-iodo-6-bromophthalimide

→

(E)-3-amino-4-(2-methoxycarbonylvinyl)-6-bromophthalimide

Ausbeute 71.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 5 hours under argon atmosphere
2. 2
   workup.STIRRINGfurther stirred for 142 hours
3. 3
   workup.STIRRINGfurther stirred for 20 hours
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with saturated brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   SonstigeThe solvent was evaporated under reduced pressure
8. 8
   Sonstigethe residue was purified by slurry

Vorschrift

3-Amino-4-iodo-6-bromophthalimide (500 mg, 1.36 mmol) was dissolved in acetonitrile (25 mL), and the solution was added with methyl acrylate (0.245 mL, 2.72 mmol), palladium acetate (24 mg, 0.11 mmol) and triethylamine (1.90 mL, 13.6 mmol), followed by stirring under reflux for 5 hours under argon atmosphere. The mixture was added with methyl acrylate (0.122 mL, 1.36 mmol), palladium acetate (24 mg, 0.11 mmol) and triethylamine (1.90 mL, 13.6 mmol) and further stirred for 142 hours. The mixture was added with methyl acrylate (0.245 mL, 2.72 mmol), palladium acetate (24 mg, 0.11 mmol) and triethylamine (0.95 mL, 6.8 mmol) and further stirred for 20 hours. The reaction mixture was added with water, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using chloroform to obtain (E)-3-amino-4-(2-methoxycarbonylvinyl)-6-bromophthalimide (313 mg, yield 71%).

Quelle