Hydrochloric Acid → 1-Bromo-4-(phenylethynyl)benzene

Participants

Reaction Steps

In a 500-mL three-neck flask were placed 14 g (51 mmol) of p-bromoiodobenzene, 5.2 g (52 mmol) of phenylacetylene, and 98 mg (0.50 mmol) of copper(I) iodide. After the atmosphere in the flask was replaced with nitrogen, 200 mL of tetrahydrofuran and 9.0 mL of triethylamine were placed in the flask, and the mixture was degassed by being stirred under reduced pressure. To this mixture was added 0.34 mg (0.50 mmol) of bis(triphenylphosphine)palladium(II) dichloride, and the mixture was stirred under a nitrogen stream at room temperature for 20 hours. After a predetermined time, 3% hydrochloric acid was added to the mixture, and an organic substance was extracted with ethyl acetate from the aqueous phase. The extracted solution combined with the organic phase was washed with brine and dried with magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina, and the filtrate was concentrated to give a solid. The obtained solid was recrystallized with hexane; thus, 7.4 g of a light-brown powder which was a product was obtained in a yield of 55%.

Provenance & Evidence