Toluene → 1-Phenylisoquinoline

Participants

Reaction Steps

3.04 g of phenylboronic acid (24.9 mmol) and 4.09 g of 1-chloroisoquinoline (25.0 mmol), 25 ml of toluene, 12.5 ml of ethanol, and 25 ml of a 2M sodium carbonate aqueous solution were introduced into a 100 ml-three-neck flask. With stirring at room temperature under a nitrogen gas flow, 0.98 g (0.85 mmol) of tetrakis-(triphenylphosphine) palladium (0) was added to the mixture. Thereafter, the resultant was stirred under reflux under a nitrogen gas flow for 8 hours. After completion of the reaction, the reaction product was cooled, and then extracted with cool water and toluene. The organic layer was washed with saline and dried with magnesium sulfate, and then the solvent was dried under reduced pressure. The residue was purified using silica gel column chromatography (eluent: chloroform/methanol: 10/1), to yield 2.20 g of 1-phenylisoquinoline (43.0% yield).

Provenance & Evidence