[S-2].[Na+].[Na+].[S].[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16]>C(O)(C)C>[Br:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])[NH2:12]A solution of sodium sulphide (31.2 g, 0.24 mol) and sulphur (7.7 g, 0.24 mol) was stirred at 80° C. for 15 minutes. Isopropanol (160 g) was subsequently added and the mixture was stirred at 75° C. for a further 15 minutes and 2-bromo-1-isopropyl-4-nitrobenzene (XI) (50 g, 0.19 mol) was finally added dropwise over a period of 30 minutes. After stirring for another 5 hours, the reaction was complete. For the work-up, the isopropanol was firstly distilled off and the remaining mixture was extracted with toluene/chlorobenzene. The combined organic phases were distilled under reduced pressure. 3-Bromo-4-isopropylaniline (42 g, 91 GC-% by area, 93% of theory) was obtained as a red oil.
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