反应 #302895

反应方程式

dimethyl disulfide

n-butyllithium

diisopropylamine

3-fluorobenzotrifluoride

→

1-fluoro-2-methylthio-3-(trifluoromethyl)benzene

溶剂

water

THF

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at this temperature for 1 h
2. 2
   workup.WAITWithin about 3 h
3. 3
   温度the reaction mixture had warmed to room temperature (RT), and it
4. 4
   温度was then once more cooled to 0° C
5. 5
   浓缩the reaction mixture was concentrated to about ¼ of its volume
6. 6
   其他dichloromethane, the phases were separated
7. 7
   洗涤the organic phase was washed successively with water, 10 percent strength hydrochloric acid, water, saturated aqueous NaHCO3 solution, water and saturated aqueous NaCl solution
8. 8
   干燥dried over sodium sulfate
9. 9
   过滤filtered
10. 10
    其他The solvent was removed

实验过程

Under an atmosphere of inert gas, 32.8 ml (1.6 M in hexane, 52.5 mmol) of n-butyllithium were added dropwise to a solution, cooled to 0° C., of 7.77 ml (55 mmol) of diisopropylamine in 100 ml of anhydrous THF, and after 10 minutes of stirring the solution was cooled to −78° C. 8.21 g (50 mmol) of 3-fluorobenzotrifluoride were added at this temperature, and the reaction mixture was stirred at this temperature for 1 h. 4.21 ml (55 mmol) of dimethyl disulfide were then added dropwise. Within about 3 h, the reaction mixture had warmed to room temperature (RT), and it was then once more cooled to 0° C. At this temperature, 10 ml of water were added dropwise, and the reaction mixture was concentrated to about ¼ of its volume. The residue was taken up in water and dichloromethane, the phases were separated and the organic phase was washed successively with water, 10 percent strength hydrochloric acid, water, saturated aqueous NaHCO3 solution, water and saturated aqueous NaCl solution and dried over sodium sulfate and filtered. The solvent was removed and the residue was rectified under reduced pressure. This gave 8 g of 1-fluoro-2-methylthio-3-(trifluoromethyl)benzene of a boiling point of 68° C. at 6 mm Hg.

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