반응 #51700

반응 방정식

3,5-Dibromopyridine

Sodium hydride

4-fluorophenol

sodium hydroxide

→

colorless oil

수율 21.0%

3-Bromo-5-(4-fluorophenoxy)pyridine

수율 21.0%

용매

water

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 1 h
2. 2
   온도the mixture was then heated at 90° C. (bath temperature) for 62 h
3. 3
   온도The mixture was cooled
4. 4
   추출extracted with diethyl ether (2×150 mL)
5. 5
   세척The combined ether extracts were washed with water
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated by rotary evaporation
9. 9
   기타The residue was purified by flash chromatography on silica gel

실험 절차

Sodium hydride (1.53 g of 80% in mineral oil, 51 mmol) was slowly added to a solution of 4-fluorophenol (5.6 g, 50 mmol) in DMF (100 mL) as it was stirred and cooled (ice water bath) under a nitrogen atmosphere. The resulting mixture was warmed to ambient temperature and stirred for 1 h. 3,5-Dibromopyridine (5.9 g, 25 mmol) was added and the mixture was then heated at 90° C. (bath temperature) for 62 h. The mixture was cooled, diluted with water (150 mL), poured into 5N sodium hydroxide (150 mL), and extracted with diethyl ether (2×150 mL). The combined ether extracts were washed with water, dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel, using 5% ethyl acetate:hexane as eluent, to yield 1.4 g (21%) of a colorless oil.

출처