反应详情

A solution of 28.3 g (112 mmole) of 2-bromophenyl-2-propanone, 14.7 ml (134 mmole) of phenylacetylene, 1.8 g (2.24 mmole) of bis(triphenylphosphine)palladium (II) chloride and 0.85 g (4.48 mmole) of copper (I) iodide in 250 ml of triethylamine under nitrogen was heated under reflux for 31/2 hours. An additional 3.6 ml of phenylacetylene, 0.36 g of palladium complex and 0.1 g copper (I) iodide were added. The mixture was heated under reflux for 31/2 hours. An additional 5.0 ml of phenylacetylene, 0.36 g of palladium complex and 0.17 g of copper (I) iodide were added. The mixture was heated under reflux for 2 hours. An additional 5.0 ml of phenylacetylene was added. The mixture was heated under reflux for 31/2 hours. The solvent was evaporated in vacuo and the residue taken up in ether. The ether was washed with water and brine, dried (K2CO3) and the solvent evaporated in vacuo. The residue was flash chromatographed on silica gel with ethyl acetate:hexane, 9:1, as eluant. The solvent was evaporated from the major compound bearing fraction to afford 21.2 g (81% yield) of 1-[2-(phenylethynyl)phenyl]-2-propanone as an oil.

1. temperatureunder reflux for 31/2 hours
2. temperatureThe mixture was heated
3. temperatureunder reflux for 31/2 hours
4. temperatureThe mixture was heated
5. temperatureunder reflux for 2 hours
6. temperatureThe mixture was heated
7. temperatureunder reflux for 31/2 hours
8. customThe solvent was evaporated in vacuo
9. washThe ether was washed with water and brine
10. dry with materialdried (K2CO3)
11. customthe solvent evaporated in vacuo
12. customchromatographed on silica gel with ethyl acetate
13. customThe solvent was evaporated from the major compound bearing fraction