Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[O-].[Na+].O.[C:18]([O:25][CH3:26])(=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21]>[Cu]Br>[C:4]([C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[CH:19]([C:18]([O:25][CH3:26])=[O:24])[C:20]([O:22][CH3:23])=[O:21])([OH:6])=[O:5]2-Chloro-4-nitrobenzoic acid (7.5 g, 37.2 mmol) was dissolved in deaerated dimethyl malonate (90 mL). Copper (I) bromide (0.54 g, 3.7 mmol) and sodium methoxide (4.83 g, 89.4 mmol) were added to the solution. The mixture was stirred at room temperature for 15 minutes, and then stirred at 70 to 75° C. overnight. After the reaction solution was allowed to return to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (7.0 g, 68%).
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