4-Iodophenol → 4-[2-(4-Methylphenyl)ethynyl]phenol

Participants

Reaction Steps

50 g of 4-ethynyltoluene, 94.6 g of 4-iodophenol and 250 ml of triethylamine were mixed at RT under a nitrogen atmosphere, and 0.35 g of triphenylphosphine and 0.2 g of copper iodide were added. 0.25 g of bis(triphenylphosphine)palladium(II) chloride were then introduced with stirring. After 30 minutes, a further 0.25 g of bis(triphenylphosphine)palladium(II) chloride and after a further 15 minutes a further 0.25 g of bis(triphenylphosphine)palladium(II) chloride were introduced, during which the temperature was held at between 40 and 55° C. After the reaction mixture had been stirred overnight, it was poured into conc. HCl/ice and subjected to conventional work-up, giving 4-p-tolylethynylphenol in the form of a solid.

Provenance & Evidence