[C:1]([C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9])#[C:2][CH2:3][CH2:4][CH3:5].[I:16]I.C(=O)(O)[O-].[Na+]>C(#N)C.CCOCC>[I:16][C:1]1[C:6]2[C:7](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:8](=[O:10])[O:9][C:2]=1[CH2:3][CH2:4][CH3:5]Methyl 2-(pent-1-ynyl)benzoate (intermediate C20.1, 3 g, 14.83 mmol), iodine (11.29 g, 44.5 mmol) and sodium bicarbonate (3.74 g, 44.5 mmol) were reacted in Acetonitrile (50 mL) for 20 min. at RT. The reaction mixture was diluted with Et2O and washed with 20% Na2S2O3aqueous and brine. The organic phase was then dried over Na2SO4 and concentrated under reduced pressure. The crude was dissolved in Et2O and purified over a silica pad to give the title compound (3.54 g, 76%) as a brown oil.
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