4-Bromotoluene → HCID 86591176, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, 33 g (0.193 mol) of 4-bromotoluene, 2.7 g (3.85 mmol) of bis(triphenylphosphine)palladium(II) dichloride and 0.735 mg (3.85 mmol) of copper Iodide were put into a 1 L 3-necked flask equipped with a stirrer, thermometer and reflux condenser, and dissolved in 500 ml of diisopropylamine. 37.9 g (0.385 mol) of trimethylsilyl acetylene was slowly dropped into the resluting solution at room temperature. The reaction mixture was slowly heated to 80° C. and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated salt was filtered off, and then the solvent was removed under a reduced pressure. The residue was dissolved in methylene chloride. The organic solution was washed with water several times and then dried with anhydrous magnesium sulfate. The solvent was removed to obtain liquid, which was purified by silica gel column chromatography using hexane as an eluent, to give 35 g (99.3% yield) of pale brown viscous liquid.

Provenance & Evidence