I[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][S:13]([C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+].C[N:29](C)C=O>[Cu]>[F:8][C:6]1[CH:7]=[C:2]([C:18]2[CH:20]=[CH:21][C:15]([S:13]([CH3:12])=[O:14])=[CH:16][CH:17]=2)[C:3]([N+:9]([O-:11])=[O:10])([NH2:29])[CH2:4][CH:5]=12-Iodo-4-fluoronitrobenzene (0.2 mole) and 4-methylsulfinylaniline (0.2 mole) are refluxed in dry dimethylformamide (300 ml.) containing copper powder (5 g) and some powdered potassium carbonate (20 g) under nitrogen for 18 hours. The suspension is filtered, and the organics are washed with water (6 times 100 ml.) in benzene (600 ml.). The benzene layer is extracted with 2.5 N HCl (7×200 ml.), and the acid layer is poured onto powdered sodium bicarbonate. The basic solution is extracted with benzene (6 times 200 ml.), the benzene layer is washed with water (3 times 100 ml.), is separated, dried (MgSO4) and filtered. Evaporation of the solvent followed by chromatography on a 2 in.×24 in. column of silica-gel (Baker), eluted with various proportions of benzene-hexane mixtures, gives pure 5-fluoro-4'-methylsulfinyl-2-nitrobiphenylamine.
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