Reaktion #49279

Reaktionsgleichung

3-Amino-4-iodo-6-bromophthalimide

2-(tributylstannyl)thiophene

ammonium fluoride

→

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

Ausbeute 87.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 12.5 hours under argon atmosphere
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by slurry
7. 7
   Sonstigepurified by preparative thin-layer chromatography (chloroform/acetonitrile=30/1)

Vorschrift

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%).

Quelle