[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:14]=1[N+:25]([O-:27])=[O:26]>CS(C)=O>[CH3:6][O:5][C:3](=[O:4])[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:14]=1[N+:25]([O-:27])=[O:26])[C:1]([O:8][CH3:9])=[O:7]Dimethyl malonate (10 ml) in 25 ml of dimethylsulfoxide was added dropwise to 3.5 g of sodium hydride suspended in 25 ml of dimethylsulfoxide and the mixture stirred at 100° C. for 10 minutes. The mixture was ,cooled to room temperature and 4.7 g of 4-fluoro-3-nitrobiphenyl in 25 ml of dimethylsulfoxide was added. The mixture was stirred at 100° C. for 2 hours, cooled and quenched with 300 ml of saturated ammonium chloride solution. The mixture was extracted three times with ethyl acetate and the combined organic layers washed with water and brine and evaporated to give a yellow oil, crude dimethyl-3-nitrobiphenyl-4-malonate.
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