I[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].CCN(CC)CC.[CH:22]1[CH:27]=CC=C[CH:23]=1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][O:13][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([C:23]#[C:22][CH3:27])[C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6]To a stirred solution of 3-iodo-4,5-dimethoxybenzoic acid (12.32 g, 40.0 mmol) in mixture of Et3N (80 mL) and benzene (80 mL) at room temperature was added CuI (760 mg, 4 mmol) followed by Pd(PPh3)4 (924 mg, 0.8 mmol, 0.02 eq.). After stirring for 2 days under propyne atmosphere (balloon) at room temperature, the solvent was removed, the residue was suspended in 1N HCl aqueous solution (300 mL) and then extracted with EtOAc (3×100 mL). The combined organic layer wash washed with brine (300 mL), dried over Na2SO4 and then concentrated in vacuo to give 3,4-dimethoxy-5-prop-1-ynylbenzoic acid (9.7 g). The product was used without further purification.
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