[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[CH:9])[CH2:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCCC)CC>[Pd].Cl[Pd]Cl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(NC(C)C)(C)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]#[C:9][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:4][CH:3]=1To a round-bottom flask equipped with a stirbar is added acetylene 4F (R=methyl) (2 g), 4-bromoanisole (3.40 g), palladium catalyst (made by mixing together 29.11 g triphenylphosphine, 3.28 g PdCl2, and 200 mL dipropylamine; refluxing the slurry for 3 hours to get a yellow slurry; cooling to room temperature; adding 3.69 g copper (II) acetate monohydrate; refluxing 1 hour; cooling and storing in the freezer) (330 mg), and diisopropylamine (80 mL). A stream of dry nitrogen is bubbled through this solution for 15 minutes to degas it, and the solution is then refluxed under a nitrogen atmosphere for 5 hours. The cooled solution is poured onto silica gel and eluted with 1:1 hexanes:ethyl acetate to give the product. The methyl group may be removed using the conditions used for deprotection of methyl ether 2F.
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