تفاعل #49281

معادلة التفاعل

water

methyl acrylate

triethylamine

methyl acrylate

triethylamine

methyl acrylate

triethylamine

3-Amino-4-iodo-6-bromophthalimide

→

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

المردود 71.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder 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
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe organic layer was washed with saturated brine
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىThe solvent was evaporated under reduced pressure
8. 8
   أخرىthe residue was purified by slurry

الإجراء التجريبي

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%).

المصدر