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 p-methylsulfinylaniline (0.2 mole) are refluxed in dry dimethylformamide (300 ml.) containing copper powder (5 gm.) and some powdered potassium carbonate (20 gm.) under nitrogen for 18 hours. The solution is filtered and the organics washed with water (6 × 100 ml.) in benzene (600 ml.). The benzene layer is extracted with 2.5 N HCl (7 × 200 ml.) and the acid layer poured onto powdered sodium bicarbonate. The basic solution is extracted with benzene (6 × 200 ml.), the benzene layer washed with water (3 × 100 ml.), 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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