Toluene → HCID 12220705, compound

Participants

Reaction Conditions

Reaction Steps

In a 100-ml round-bottomed flask equipped with a magnetic stirrer, were added 1.0 g (3.26 mmol) of 5-bromonaphthacene, 23 mg (0.0326 mmol) of dichlorobis(triphenylphosphine)palladium(II) catalyst and 12 ml of toluene. A solution containing 0.69 g (6.51 mmol) of sodium bicarbonate in 4 ml of water was added to the flask. The mixture was degassed via nitrogen purge for 10 minutes. A solution of 0.417 g (3.42 mmol) of phenylboronic acid in 12 ml of ethanol was then added to the flask, and the reaction mixture was heated to 75° C. and stirred overnight for 15 hours. The resulting reaction mixture contained yellow and white solids that were dissolved by the addition of toluene and water. The mixture was transferred to a 100-ml separatory funnel and the aqueous layer was extracted three times with 15 ml of toluene. After the toluene layer was back-extracted once with distilled water, it was stirred over sodium sulfate for one hour and filtered. Charcoal (2 g) was added to the toluene layer and stirred for a minimum of 2 hours. The charcoal was filtered off and the solvent was removed by rotary evaporation. The product was dried at room temperature under vacuum (product sublimed at higher temperatures). 5-Phenylnaphthacene was obtained in 93% yield (0.92 g) and used without further purification.

Provenance & Evidence