4-Iodoanisole (98%,  Purchased from Sigma-Aldrich)
Propargyl Alcohol (99%, Purchased from Sigma-Aldrich)
Copper(I) Iodide (99.5% Purum, Purchased from Sigma-Aldrich)
Bis(triphenylphosphine)palladium(II) dichloride (> 99% Pure, Purchased from Sigma-Aldrich)
Triethylamine (99%, Purchased from ACROS)

 

To a 250 mL round bottom flask equipped with stirbar was added 4-iodoanisole, ( 4.68 g, 0.020 mol, 1 equiv.) and Et₃N (150 mL, 0.134 M in the iodide).  The solution was placed under a nitrogen atmosphere via a gas inlet adapter. To this solution was added PdCl₂(PPh₃)₂ (0.702 g, 0.001 mol, 0.05 equiv.) and CuI (0.191 g, 0.001 mol, 0.05 equiv) all at once turning the solution yellow. Propargyl alcohol (1.46 g, 0.026 mol, 1.3 equiv) was then added all at once, turing the solution a cloudy green. The solution was stirred for 18 hours at room temperature and monitored by TLC (8:2 Hex: EtOAc). Upon completion of this time, the solution was filtered through Celite^®, eluting with ethyl acetate. The filterate was then further diluted with  EtOAc (≈50 mL) and deionized water (≈100 mL) and the layers were seperated. The aqueous layer was extracted three times with EtOAc. The combine organic layers were dried with Na₂SO₄ and the solvent was removed in vacuo yielding a thick dark liquid. Purification was accomplished by flash column chromoatgraphy (Gradient 9:1 Hex: EtOAc to 8:2) affording pure 6r as a tan powdery solid (2.75 g, 85% yield). 

¹H NMR (CDCl₃, 300 MHz) d ppm 1.65 (t, J = 6.14 Hz, 1 H) 3.81 (s, 3 H) 4.48 (d, J = 6.14 Hz, 2 H) 6.84 (d, J = 9.10 Hz, 2 H) 7.38 (d, J = 8.77 Hz, 2 H) ¹³C NMR (CDCl₃, 101 MHz) d ppm 51.85 (CH₂) 55.53 (CH₃) 85.82 (C) 86.22 (C) 114.21 (CH) 114.91 (C) 133.44 (CH) 159.95 (C)

Belot, A.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem. Int . Ed. 2009 , 48 , 8923.