N([O-])=O.[Na+].[Cl:5][C:6]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([Cl:14])[C:7]=1N.Cl.[CH3:16][S:17]SC>O.C(O)(=O)C.[Cu]>[Cl:5][C:6]1[C:7]([S:17][CH3:16])=[C:9]([Cl:14])[CH:10]=[CH:11][C:12]=1[CH3:13]A solution of sodium nitrite (12.0 g) in water was added to a stirred suspension of 2,6-dichloro-3-methylaniline (30.0 g) in a mixture of glacial acetic acid and concentrated hydrochloric acid. While maintaining the temperature below 10° C. The mixture was stirred at 0° C. for three quarters of an hour then added to a mixture of dimethyl disulphide (20 ml) and copper powder (0.25 g) in glacial acetic acid. The mixture was stirred for 4 hours and extracted with ether. The organic layer was washed with aqueous sodium carbonate (2M), water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 2,4-dichloro-3-(methylsulphenyl)toluene (27.2 g) as a red liquid NMR (CDCl3) 2.4(s,3H), 2.45(s,3H), 7.15(d,1H), 7.3(d,1H).
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