تفاعل #49279

معادلة التفاعل

3-Amino-4-iodo-6-bromophthalimide

2-(tributylstannyl)thiophene

ammonium fluoride

→

3-amino-4-(thiophen-2-yl)-6-bromophthalimide

المردود 87.3%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder reflux for 12.5 hours under argon atmosphere
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   أخرىThe solvent was evaporated under reduced pressure
6. 6
   أخرىThe residue was purified by slurry
7. 7
   أخرىpurified by preparative thin-layer chromatography (chloroform/acetonitrile=30/1)

الإجراء التجريبي

3-Amino-4-iodo-6-bromophthalimide (100 mg, 0.273 mmol) was dissolved in THF (5 mL), and the solution was added with 2-(tributylstannyl)thiophene (0.173 mL, 0.546 mmol) and bis(triphenylphosphine)dichloropalladium (15 mg, 0.022 mmol), followed by stirring under reflux for 12.5 hours under argon atmosphere. The reaction mixture was added with 10% aqueous ammonium fluoride solution, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by slurry using hexane, then purified by preparative thin-layer chromatography (chloroform/acetonitrile=30/1) to obtain 3-amino-4-(thiophen-2-yl)-6-bromophthalimide (77 mg, yield 87%).

المصدر