反应详情

Combine 2-methyl-6-fluoro-pyridine (19.6 g, 176 mmol), 1,1′-azobis-(cyclohexane-carbonitrile) (0.431 g, 1.77 mmol), and freshly recystallized N-bromo-succinimide (32.96 g, 185 mmol) in carbon tetrachloride (200 mL) and stir in a 1000 mL flask while radiating with UV light for 18 h. Allow to cool, then filter to remove succinimide and wash with dilute Na2S2O3 solution. Dry over Na2SO4, filter and evaporate to give an amber oil. Purify by silica gel chromatography, eluting with 0-30% EtOAc/hexanes to obtain 12.3 g (37%) of a clear oil. MS 100% (m/e) 190 (EI); 1H NMR (DMSO, 400 MHz): δ 8.03-7.95 (m, 1H), 8.03-7.95 (m, 1H), 7.48 (dd, 1H, J=7.5, 2.6 Hz), 7.11 (dd, 1H, J=7.9, 2.6 Hz), 4.63 (s, 2H).

1. temperatureto cool
2. filtrationfilter
3. customto remove succinimide
4. washwash with dilute Na2S2O3 solution
5. dry with materialDry over Na2SO4
6. filtrationfilter
7. customevaporate
8. customto give an amber oil
9. customPurify by silica gel chromatography
10. washeluting with 0-30% EtOAc/hexanes