反应详情

To a 500 mL 3-neck round-bottom flask was added 4-chloro-3-nitro-phenol (10 g, 0.058 mol), potassium carbonate (20 g, 0.14 mol), bromochloroethane (34.5 g, 0.24 mol) and 2-butanone (200 mL). The mixture was mechanically stirred and heated to reflux for 20 hours under nitrogen then allowed to cool to room temperature and the solids were filtered. The solvent was evaporated under vacuum and the oil dissolved in diethyl ether (300 mL) and washed with 10% sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent removed under vacuum. The product was dissolved in 1:1 methylene chloride-hexanes and filtered through a short pad silica. Upon concentration and standing 12.9 g (94.8.% %) of light yellow crystalline solid was afforded: mp 46°-48° C.; MS EI m/e 235, 237, 239 (M+); 1H NMR (400 MHz, DMSO-d6) δ 3.95 (t, 2H, J=5.2 Hz), 4.36 (t, 2H, J=5.2 Hz), 7.32 (dd, 1H, J=3.2, J=8.9 Hz), 7.66, (d, 1H, J=9 Hz), 7.69, (d, 1H, J=3.2 Hz).

1. temperatureheated
2. temperatureto reflux for 20 hours under nitrogen
3. filtrationthe solids were filtered
4. customThe solvent was evaporated under vacuum
5. dissolutionthe oil dissolved in diethyl ether (300 mL)
6. washwashed with 10% sodium hydroxide
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe solvent removed under vacuum
10. dissolutionThe product was dissolved in 1:1 methylene chloride-hexanes
11. filtrationfiltered through a short pad silica
12. concentrationUpon concentration
13. customwas afforded