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0 °C

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).

1. temperatureWhile maintaining the temperature below 10° C
2. stirringThe mixture was stirred for 4 hours
3. extractionextracted with ether
4. washThe organic layer was washed with aqueous sodium carbonate (2M), water
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customThe filtrate was evaporated to dryness