反应详情

温度

-78 °C

Acetonitrile (0.97 g, 23.7 mmol) is added dropwise to a solution of lithium diisopropylamide (two molar in hydrocarbons, 10.9 mL, 21.8 mmol) in tetrahydrofuran at -78° C. The reaction mixture is stirred at -78° C. for 30 minutes, treated with a solution of 3,4,5-trichloro-2-thiophenecarbonitrile (3.87 g, 18.2 mmol) in tetrahydrofuran, stirred for 30 minutes at -78° C., warmed to room temperature over 45 minutes, quenched with saturated ammonium chloride solution and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a red solid. A mixture of the red solid and 1-bromo-3,3,3-trifluoroacetone (1.95 mL, 18.7 mmol) in acetic acid is refluxed for three hours and 30 minutes, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated .in vacuo to obtain a red solid. Flash chromatography of the solid using silica gel and a 15% ethyl acetate in hexane solution gives the title product as a white solid (0.49 g, 7.8%, mp 220°-221° C.).

1. stirringstirred for 30 minutes at -78° C.
2. temperaturewarmed to room temperature over 45 minutes
3. customquenched with saturated ammonium chloride solution
4. extractionextracted with ether
5. washThe combined organic extracts are washed sequentially with water and brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customto obtain a red solid
9. temperatureis refluxed for three hours and 30 minutes
10. extractionextracted with ether
11. washThe combined organic extracts are washed sequentially with water and brine
12. dry with materialdried over MgSO4
13. concentrationconcentrated .in vacuo
14. customto obtain a red solid