Réaction #49275

Équation de réaction

ammonium chloride

phenylboronic acid

chloroform methanol

3-Amino-4-iodo-6-bromophthalimide

→

3-amino-4-phenyl-6-bromophthalimide

Rendement 66.0%

3-amino-4,6-diphenylphthalimide

Rendement 11.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   AutreThe solvent was evaporated under reduced pressure
5. 5
   AutreThe residue was purified by slurry

Mode opératoire

3-Amino-4-iodo-6-bromophthalimide (80.0 mg, 0.218 mmol) was dissolved in THF (5.6 mL), and the solution was added with phenylboronic acid (80 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol) and copper(I) thiophene-2-carboxylate (125 mg, 0.65 mmol), followed by stirring at room temperature for 14 hours under argon atmosphere. The reaction mixture was added with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by slurry using isopropylether, then by preparative thin-layer chromatography (chloroform/methanol=60/1) to obtain 3-amino-4-phenyl-6-bromophthalimide (46 mg, yield 66%) and 3-amino-4,6-diphenylphthalimide (7.6 mg, yield 11%).

Source