Reaction #49275

Reaction equation

ammonium chloride

phenylboronic acid

chloroform methanol

3-Amino-4-iodo-6-bromophthalimide

→

3-amino-4-phenyl-6-bromophthalimide

Yield 66.0%

3-amino-4,6-diphenylphthalimide

Yield 11.0%

Solvents

THF

Conditions

Workup

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

Procedure

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