반응 #62547

반응 방정식

potassium fluoride

4-chloro-3-nitropyridine

potassium dihydrogen phosphate

→

4-fluoro-3-nitropyridine

수율 52.0%

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   workup.DISTILLATIONthe solvent reduced to half its volume by distillation under an atmosphere of nitrogen
2. 2
   온도cooled
3. 3
   추출The resulting mixture was extracted with ethyl acetate
4. 4
   세척The organic phase was washed three times with water
5. 5
   건조brine before being dried over anhydrous magnesium sulphate
6. 6
   기타The solvent was removed in vacuo

실험 절차

Anhydrous potassium fluoride (5.5 g, 93 mmol) was suspended in anhydrous dimethylsulfoxide (200 ml) and the solvent reduced to half its volume by distillation under an atmosphere of nitrogen. The resulting suspension was cooled to room temperature and 4-chloro-3-nitropyridine (14 g, 88 mmol) was added. The reaction mixture was stirred at 120° C. for three hours under an atmosphere of nitrogen, cooled and then poured into a saturated aqueous solution of potassium dihydrogen phosphate. The resulting mixture was extracted with ethyl acetate. The organic phase was washed three times with water and then brine before being dried over anhydrous magnesium sulphate. The solvent was removed in vacuo to yield as an oil, 4-fluoro-3-nitropyridine (6.5 g), (δ(CDCl3) 7.32 (1H, 4 lines), 7.86 (1H, t, J=5 Hz) and 8.29 (1H, d, J=9 Hz), represented by the structural formula: ##STR21##

출처