Phenylacetylene → 1-[5-Methoxy-2-(phenylethynyl)phenyl]-2-propanone

Participants

Reaction Steps

A solution of 5.5 g (18.9 mmole) 2-iodo-5-methoxyphenyl-2-propanone (18.9 mmole), 4.15 ml (37.8 mmole) of phenylacetylene, 0.037 g cuprous iodide (1 mole percent) and 0.066 g of bis(triphenylphosphine)palladium (II) chloride (5 mole percent) in 60 ml of triethylamine was stirred for 18 hours under N2 at room temperature. The mixture was partitioned between water and ether. The ether layer was washed successively with cold hydrochloric acid solution, washed and brine. It was dried over MgSO4 and the solvent evaporated in vacuo to give 5.6 g (100% yield) of brown crystals. Recrystallization from methylcyclohexane afforded pure 1-[5-(methoxy)-2-(phenylethynyl)phenyl]-2-propanone, mp 60°-62° C.

Provenance & Evidence