Ethanol → 5-Phenyloxindole

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-oxindole (5 g, 23.5 mmol) was dissolved in 110 mL of toluene and 110 mL of ethanol with stirring and a little heating. Tetrakis(triphenylphosphine)-palladium(0) (1.9 g, 1.6 mmol) was added followed by a 2 M aq. solution of sodium carbonate (40 mL, 80 mmol). To this mixture benzene boronic acid (3.7 g, 30.6 mmol) was added and the mixture was heated in a 100° C. oil bath. After 12 h, the reaction was diluted with ethyl acetate (500 mL), washed with saturated aq. sodium bicarbonate (200 mL), water (200 mL), 1 N HCl (200 mL) and brine (200 mL). The organic layer was dried with magnesium sulfate and concentrated to afford a brown solid. Trituration with dichloromethane and filtering afforded 3.8 g (77%) of a tan solid.

Provenance & Evidence