Water → 2-Bromo-3,4-dimethylaniline
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[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.O.O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10][Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.O.O.Cl[Sn]Cl.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10]To a solution of 2-bromo-3,4-dimethylnitrobenzene (1.0 g, 4.35 mmole) in 10 mL DMF was added SnCl2.2H2O (4.92 g, 21.8 mmole). This solution was stirred overnight at room temperature 50 mL of H2O was added and the pH was adjusted to 8 with the addition of sat. NaHCO3 and extracted with 150 mL of EtOAC. The organic layer was dried over Na2SO4, filtered and evaporated yielding 2-bromo-3,4-dimethylaniline which was used as is in the conversion to 2-bromo-3,4-dimethyliodobenzene in a similar manner to that of Example 86. Compound 102 was prepared from 2-bromo-3,4-dimethyliodo-benzene using procedures similar to those of Examples 25 and 40. MS (ion spray): m/z 314.0/316.1 (M−H); 316.1/318.0 (M+H). 1H NMR: (DMSO-d6, 400 MHz) δ 7.37 (d, 1H), 7.15 (d, 1H), 2.43 (s, 3H), 2.37 (s, 3H).
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