Phenylacetylene → HCID 70974553, compound

Participants

Reaction Steps

A mixture of 1,3-dibromo-5-nitrobenzene (0.56 g, 2.00 mmol), bis(triphenylphosphine)palladium(II) chloride (0.10 g, 0.14 mmol) and copper(I) iodide (0.027 g, 0.14 mmol) in Et3N was degassed (three times). Phenylacetylene (0.50 g, 4.88 mmol) was added and mixture was stirred overnight. The reaction mixture was filtered through a celite pad and the pad was rinsed with CH2Cl2. The filtrate was washed with brine and the organic layer was dried with (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (Dichloromethane;Hexane=1:10) to afford ((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))dibenzene (0.33 g, 51% yield): 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, J=1.3 Hz, 2H), 7.96 (t, J=1.3 Hz, 1H), 7.56 (m, 4H), 7.40 (m, 6H).

Provenance & Evidence