反应 #172405

反应方程式

water hydrochloric acid

3-bromopyridin-2(1H)-one

1-fluoro-2,5-dimethyl-4-nitrobenzene

potassium carbonate

→

3-Bromo-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

溶剂

dimethyl sulphoxide

dimethyl sulphoxide

反应条件

后处理

1. 1
   温度After cooling
2. 2
   萃取The mixture is extracted with ethyl acetate
3. 3
   其他the phases are separated
4. 4
   萃取the aqueous phase is once more extracted with ethyl acetate
5. 5
   洗涤The combined organic phases are then washed with water
6. 6
   其他The phases are separated
7. 7
   干燥the organic phase is dried over sodium sulphate
8. 8
   浓缩After concentration under reduced pressure
9. 9
   其他the residue is purified by chromatography on silica gel (dichloromethane
10. 10
    其他the solvents are removed
11. 11
    其他the residue is triturated with diethyl ether

实验过程

150 g (750 mmol) of 3-bromopyridin-2(1H)-one (O. S. Tee, M. Pavent, J. Am. Chem. Soc. 1982, 104, 4142-4146.) and 207 g (1.50 mol) of potassium carbonate are dissolved in 2.9 l of dimethyl sulphoxide and heated to 120° C. At this temperature, a solution of 317 g (750 mmol) of 1-fluoro-2,5-dimethyl-4-nitrobenzene in 700 ml of dimethyl sulphoxide is added dropwise over a period of 60 min, and the mixture is stirred at 120° C. for 3.5 h. After cooling, the reaction solution is stirred into a water/hydrochloric acid mixture. The mixture is extracted with ethyl acetate, the phases are separated and the aqueous phase is once more extracted with ethyl acetate. The combined organic phases are then washed with water. The phases are separated, and the organic phase is dried over sodium sulphate. After concentration under reduced pressure, the residue is purified by chromatography on silica gel (dichloromethane, then ethyl acetate/dichloromethane 1:20). The product-containing fractions are combined, the solvents are removed and the residue is triturated with diethyl ether. This gives 112 g (46% of theory) of the desired compound.

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