[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH:13]([CH3:15])[CH3:14].Cl[Sn]Cl.C([O-])(O)=O.[Na+].NC1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1.C1C[O:42][CH2:41][CH2:40]1>O>[Br:38][C:5]1[CH:4]=[C:3]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][C:41](=[O:42])[CH3:40]5.5 g (27.4 mmol) 2-Chloro-1-isobutoxy-4-nitro-benzene was dissolved in 150 ml THF and 30 ml water. After addition of 36.4 g (192 mmol) SnCl2 the reaction mixture was refluxed for 15 minutes. NaHCO3 solution was added, the mixture was extracted with ethyl acetate, dried and concentrated. The crude aniline (5.2 g, 95%) was used without further purification. 2.0 g (10.0 mmol) of the aniline were treated with 1.78 g (10.0 mmol) NBS in 60 ml THF for 20 hours at room temperature. Extraction with ethyl acetate, washings with Na2S2O3 and Na2CO3, drying of the organic phase and removal of solvent yielded 2.75 g of the desired 2-Bromo-5-chloro-4-isobutoxy-aniline.
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