[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].O.O.O.C([O-])(=O)C.[Na+].[I:18]Cl.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(OCC)C>[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([I:18])[C:3]=1[NH2:4]A solution of 2-fluoro-4-methylaniline (1.0 g, 8 mmol) (bought from Avocado, Lancaster or Aldrich) in glacial acetic acid (10 ml) was treated with sodium acetate trihydrate (2.2 g, 16 mmol) then iodine monochloride (1.3 g). After 30 min at room temperature aqueous sodium bicarbonate/sodium sulfite and diethyl ether were added, and the organic phase was dried (MgSO4), evaporated and chromatographed on silica eluting with 0 to 30% ethyl acetate in hexane to give the title compound, 370 mg.
Loading…
