반응 #431190

반응 방정식

2-chloro-4-hydroxymethylpyridine

NBS

K2CO3

NBS

Na2CO3

→

title compound

수율 67.0%

2-Chloro-4-pyridinecarboxaldehyde

수율 67.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도was refluxed for 3 h
2. 2
   온도heating
3. 3
   온도The reaction mixture was cooled
4. 4
   여과filtered through a pad of celite
5. 5
   농축concentrated under reduced and
6. 6
   기타chromatographed with 0.5-4% CH3OH/CH2Cl2
7. 7
   세척The combined fractions were washed with NaHCO3 (sat.), 10% Na2S2O3, and NaCl (sat.)
8. 8
   기타dried
9. 9
   여과filtered
10. 10
    기타evaporated

실험 절차

A suspension of 2-chloro-4-hydroxymethylpyridine (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2CO3 (11.75 g, 97.1 mmol) in ethyl acetate was refluxed for 3 h. Another portion of NBS (14.9 g, 83.9 mmol) and Na2CO3 (12.0 g, 114 mmol) was added and heating was continued another 3.5 h. The reaction mixture was cooled, filtered through a pad of celite, concentrated under reduced and chromatographed with 0.5-4% CH3OH/CH2Cl2. The combined fractions were washed with NaHCO3 (sat.), 10% Na2S2O3, and NaCl (sat.), dried, filtered and evaporated to give the title compound as a light yellow solid (5.3 g, 67% yield). 1H NMR (CDCl3): δ 10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H, J=5.0 Hz).

출처