4-Chlorophenylacetylene

9.5 g (0.04 mol) of 4-chloroiodobenzene and 4.2 g (0.05 mol) of 3-methylbutynol, 0.3 g of diphenylphosphine palladium dichloride Pd[(C6H5)3P]2Cl2, and 100 ml of triethylamine were mixed, and the mixture was allowed to mix and stir under the protection of nitrogen for 15 minutes. While keeping the mixture in nitrogen atmosphere, 180 mg of cuprous iodide was added. A precipitate was observed to form almost immediately. The mixture was stirred at room temperature for about 12 h. The mixture was diluted by adding ether (200 ml) and filtered. The resulting filtrate was removed from the filtrate by evaporation under reduced pressure to remove almost all the solvent and the residue was diluted with 150 ml of toluene. To the resulting solution 2.5 g of NaOH powder was added and heated to reflux the reaction for 4 hours. After filtration while hot, the solvent was removed from the filtrate by evaporation under reduced pressure. 4.6 g of 4-chlorophenylacetylene in the form of a waxy solid was obtained.