[CH2:1]([OH:4])[C:2]#[CH:3].[F:5][C:6]1[CH:7]=[C:8](I)[CH:9]=[CH:10][CH:11]=1>[Cu](I)I.C(NCC)C>[F:5][C:6]1[CH:11]=[C:10]([C:3]#[C:2][CH2:1][OH:4])[CH:9]=[CH:8][CH:7]=1A mixture of propargyl alcohol (0.200 g, 5.4 mmol), 3-fluoro iodobenzene (0.63 ml, 5.4 mmol), copper iodide (0.103 g, 0.54 mol), dichlorobis (triphenylphosphine) palladium (II) (0.190 g, 0.3 mmol), diethylamine (10 ml) was degassed for 10 min. and stirred for 20 hrs at 25-25° C. Excess of diethyl amine was distilled off under vacuum. The residue was diluted with water (10 ml) and extracted with ethyl acetate. The organic layer was washed with brine solution and dried over Na2SO4. The solvent was evaporated and the crude product was purified by column chromatography (10% Ethyl acetate in hexane) to obtain pure 3-(3-fluoro-phenyl)-prop-2-yn-1-ol (0.750 g, 93%).
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