N[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:28].[K+]>O>[F:11][C:10]([F:13])([F:12])[C:9]([C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[I:28])([OH:18])[C:14]([F:17])([F:16])[F:15]To compound 1 (2 g, 7.32 mmol) in suspension in distilled water (20 mL) cooled in a ice-bath was added sulfuric acid (0.5 mL). Sodium nitrite (505 mg, 7.32 mmol) dissolved in water (2.5 mL) was added dropwise and another 0.5 mL sulfuric acid was added. The mixture was stirred at 0° C. until complete dissolution of the suspension (ca 30 min). The solution was added dropwise over 30 min to ice cooled potassium iodide (1.46 g, 8.78 mmol) dissolved in distilled water (5 mL). The reaction mixture when then heated at 80° C. until nitrogen formation stops (ca 30 min). After return to room temperature, the red suspension was filtered, washed with water and dissolved in diethylether (50 mL). It was washed with water (20 mL) and 1N hydrochloric acid (20 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was chromatographied on a silica gel column with heptane/chloroform (1/1) as eluent to give 1.98 g (5.16 mmol, 71% yield) of a yellow oil which solidifies at 4° C. over night.
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