3-(3,5-dichlorophenyl)prop-2-yn-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,5-dichloroiodobenzene (2.50 g), copper(I) iodide (34.9 mg), triphenylphosphine (120 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (189 mg), propargyl alcohol (0.596 ml), diisopropylethylamine (6.38 ml) and tetrahydrofuran (50 ml) was stirred at room temperature for 4 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-80:20) to give the object product (1.73 g) as a brown solid. the mixture was extracted with ethyl acetate washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-80:20)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,5-dichloroiodobenzene (2.50 g), copper(I) iodide (34.9 mg), triphenylphosphine (120 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (189 mg), propargyl alcohol (0.596 ml), diisopropylethylamine (6.38 ml) and tetrahydrofuran (50 ml) was stirred at room temperature for 4 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-80:20) to give the object product (1.73 g) as a brown solid. the mixture was extracted with ethyl acetate washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-80:20)