I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N+:12]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>N1C=CC=CC=1.[Cu].O>[C:5]([C:4]1[CH:3]=[C:2]([O:21][C:17]2[CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=1)([O:7][CH3:8])=[O:6]A solution of methyl 3-iodobenzoate (2.54 g), 3-nitrophenol (1.48 g), and K2CO3 (3.97 g) in 60 mL of pyridine was warmed to 100° C. under nitrogen atmosphere. Copper powder (1.84 g) was added, and the reaction mixture was heated to reflux. After 22 h, The reaction was cooled to room temperature and poured into ethyl acetate and water. The organic layer was washed twice with 10% aq. HCl solution, then with sat. aq. NaHCO3 solution, then with brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (CH2Cl2) provided the product as a yellow oil.
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