反应详情

N-Bromosuccinimide (0.61 g, 3.4 mmol) and VAZO (0.10 g, 0.41 mmol) were added to a solution of 4-fluoro-2-iodotoluene (0.75 g, 3.2 mmol) in carbon tetrachloride (45 mL). The resulting suspension was stirred and heated under reflux for 18 hours. It was then cooled and filtered, the solid was rinsed with carbon tetrachloride (5 mL), and the combined filtrates were concentrated under reduced pressure. The residue was purified by flash column chromatography (eluting with hexanes) to provide 322 (0.58 g, 58% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.51 (dd, J=8.0, 2.5 Hz, 1H); 7.38 (dd, J=8.4, 5.7 Hz, 1H); 7.00 (dt, J=8.2, 2.7 Hz, 1H); 4.54 (s, 2H).

1. temperatureheated
2. temperatureunder reflux for 18 hours
3. temperatureIt was then cooled
4. filtrationfiltered
5. washthe solid was rinsed with carbon tetrachloride (5 mL)
6. concentrationthe combined filtrates were concentrated under reduced pressure
7. customThe residue was purified by flash column chromatography (eluting with hexanes)