Phenylboronic Acid → HCID 67521052, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 81 (318 mg; 0.85 mmol) in toluene (8.5 mL) was added a solution of phenylboronic acid (152 mg; 1.12 mmol) in ethanol (5.6 mL). Bis(triphenylphosphine)palladium(II) dichloride (32 mg; 0.05 mmol) was then added, followed by the addition of aqueous saturated sodium bicarbonate (3.3 mL). The reaction was placed under a nitrogen atmosphere and then heated at 80° C. for 17 hours. After cooling to room temperature, the reaction was extracted with dichloromethane (70 mL) and washed with aqueous hydrochloric acid (40 mL; 2N), water (40 mL), and aqueous saturated sodium chloride (40 mL). The dichloromethane extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by a silica gel chromatography (9% to 16% ethyl acetate in hexanes gradient) to yield the title compound as a white solid (217 mg).

Provenance & Evidence