反应详情

A mixture of p-bromonitrobenzene (2.02 g, 10 mmol), bis(triphenylphosphine)palladium(II) chloride (0.2 g, 0.3 mmol), and copper(1) iodide (0.05 g, 0.3 mmol) in 40 ml of N,N-diisopropylamine was degassed by freeze/pump/thaw technique (three times). Trimethylsilylacetylene (1.2 g, 12 mmol) was added and the mixture was refluxed for 12 hours. After removal of amine by rotary evaporation, the residue was dissolved in CH2Cl2 and washed with water. The organic layer was dried (Na2SO4), filtered, and rotary evaporated. The residue was purified by column chromatography (EtOAc/hexanes, 1:10) to afford 4-(trimethylsilylethynyl)nitrobenzene (1.53 g, 70%). (Procedure adapted from Takahashi, S; Kuroyama, Y; Sonogashira, K; Hagihara, N. Synthesis, 1980, 627.)

1. customwas degassed by freeze/pump/thaw technique (three times)
2. temperaturethe mixture was refluxed for 12 hours
3. customAfter removal of amine
4. customby rotary evaporation
5. dissolutionthe residue was dissolved in CH2Cl2
6. washwashed with water
7. dry with materialThe organic layer was dried (Na2SO4)
8. filtrationfiltered
9. customThe residue was purified by column chromatography (EtOAc/hexanes, 1:10)