反应详情

温度

0 °C

2-Fluoro-5-(methylsulfonyl)aniline (Intermediate 57; 500 mg; 2.64 mmol) was treated with a 5 N solution of hydrochloric acid in water (8.98 ml; 44.92 mmol) and the solution cooled to 0° C. The solution was treated with sodium nitrite (219 mg; 3.17 mmol) and stirred at 0° C. for 30 minutes, then treated with a solution of potassium iodide (4.39 g; 26.43 mmol) in water (8 mL) and stirred at RT for 1 hour. EtOAc was added, the phases were separated and the organic phase was washed with a saturated sodium thiosulfate solution twice, then with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a white solid.

1. stirringstirred at RT for 1 hour
2. customthe phases were separated
3. washthe organic phase was washed with a saturated sodium thiosulfate solution twice
4. customThe organic phase was dried on MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a residue which
8. customwas purified by by flash column chromatography
9. washeluting with cyclohexane containing
10. temperatureincreasing amounts of EtOAc