Phenylboronic Acid → 6-Phenyl-1,3-dihydro-indol-2-one

Participants

Reaction Steps

6-Bromooxindole (800 mg, 3.8 mmol), (prepared as described for the starting material in Example 62), phenylboronic acid (500 mg, 4.1 mmol) sodium hydrogen carbonate (saturated aqueous solution, 50 ml) and 1,2-dimethoxyethane (100 ml) were mixed together and the solution was degassed using alternatively vacuum and argon. Tetrakis(triphenylphosphine)palladium(0) (50 mg) was added and the solution degassed again before heating it to reflux for 8 hours. The reaction mixture was evaporated to dryness using a rotary evaporator and the solid residue partitioned between water (75 ml) and ethyl acetate (100 ml). The aqueous phase was reextracted with more ethyl acetate (100 ml×3), the organic phases were combined, washed with brine and passed directly through a short plug of silica to remove the baseline impurities. The solvent was evaporated and the solid was triturated in ether and filtered to give 6-phenyloxindole as a pink solid (375 mg, 60%).

Provenance & Evidence