Tetrahydrofuran → 1-bromo-4-(phenylethynyl)benzene

Participants

Reaction Steps

Into a 1000-mL three-neck flask were added 28.3 g (0.10 mol) of p-bromoiodobenzene, 10.2 g (0.10 mol) of phenylacetylene, 701 mg (1 mmol) of bis(triphenylphosphine)palladium(II)dichloride, and 190 mg (1 mmol) of copper(I) iodide, and nitrogen substitution was carried out. Then, 350 mL of tetrahydrofuran and 18 mL of triethylamine were added thereto, and the mixture was stirred at room temperature for 12 hours. After the reaction, the reaction mixture was washed with a 3% hydrochloric acid aqueous solution, and an aqueous phase was extracted with ethyl acetate. The extract combined with an organic phase was washed with a saturated saline solution and then dried with magnesium sulfate. The mixture was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855, the same product was used hereinafter), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135, the same product was used hereinafter), and alumina, and a solid obtained by the concentration of the filtrate was recrystallized with hexane to give 15 g of the target product as a solid at a yield of 58%.

Provenance & Evidence