Water → Benzene, 1-bromo-3-fluoro-4-(methylthio)-2-(trifluoromethyl)-

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A solution of sodium nitrite (11.2 g) in concentrated sulphuric acid was added to a stirred cooled suspension of 4-bromo-2-fluoro-3-trifluoromethylaniline (40 g) in glacial acetic acid while maintaining the temperature below 5° C. The mixture was stirred at 5° C. for one and a half hours. The resultant mixture was added gradually to a mixture of dimethyl disulphide (20 ml) and copper power (0.224 g) in glacial acetic acid at 45° C. It was stirred and heated at 70° C. for 3 hours. It was cooled, poured into water, extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and purified by column chromatography eluted with petroleum spirit (b.p. 60°-80° C.) to give 6-bromo-2-fluoro-3-(methylsulphenyl)benzotrifluoride (30.6 g) as an orange oil NMR (CDCl3) 2.45(s,3H), 7.25(t,1H), 7.5(d,1H).

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