[CH2:1]([OH:4])[C:2]#[CH:3].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1I.CN(C)C=O.C(N(CC)CC)C>[Cl-].[Na+].O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[C:3]#[C:2][CH2:1][OH:4]To a microwave vial were added propargyl alcohol (0.19 ml; 3.3 mmol), 1,3,5-trichloro-2-iodo-benzene (0.50 g; 1.6 mmol), N,N-dimethylformamide (6 ml), triethylamine (4 ml), bis(triphenylphosphine) palladium(II) chloride (0.11 g; 0.16 mmol) and copper iodide (31 mg; 0.16 mmol). The mixture was degassed under argon. The orange solution was heated in the microwave at 120° C. during 25 min. The mixture obtained was poured in brine and extracted three times with dichloromethane. Organic were combined, dried over sodium sulfate and evaporated under reduced pressure to provide the crude which was subject to flash chromatography (eluant: c-hexane/ethyl acetate 8:2). 290 mg (75% of theory) of 3-(2,4,6-trichloro-phenyl)-prop-2-yn-1-ol was obtained as a yellow solid.
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