Phenylacetylene → HCID 21705263, compound

Participants

Reaction Steps

A solution of 3,3'-dibromobenzil (5.0 g, 0.0136 mol) and phenylacetylene (3.47 g, 0.0340 mol) in triethylamine (30 mL) is deaerated by bubbling nitrogen through the solution for ten minutes. (PPh3)2PdCl2 (0.067 g, 0.0001 mol) is then added, and the reaction mixture heated at reflux overnight. The mixture is concentrated to dryness, then taken up in CH2Cl2 (100 mL), washed sequentially with 1 M HCl, saturated aqueous NaHCO3 and dried (Na2SO4), then concentrated, giving 3.67 g (66 percent) product as a white solid: m.p. 144° C. to 145° C.; 1H NMR (CDCl3) δ 8.12 (s, 2H), 7.96 (d, J=7.9 Hz, 2H), 7.81 (d, J=7.7 Hz, 2H), 7.52 (m, 6H), 7.36 (m, 6H); 13C NMR (CDCl3) δ 192.83, 137.40, 132.82, 131.52, 129.04, 128.58, 128.25, 124.50, 122.37, 91.11, 87.62.

Provenance & Evidence