반응 #8208

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2-bromo-4,6-difluoro-N-carbethoxy aniline

triethyl amine

Trimethylsilyl acetylene

→

2-(trimethylsilylethynyl)-4,6-difluoro-N-carbethoxyaniline

수율 71.0%

용매

CH3CN

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후처리

1. 1
   기타purged with N2
2. 2
   workup.ADDITIONare added
3. 3
   세척rinsed in with 100 mL of CH3CN
4. 4
   기타reaction
5. 5
   온도is refluxed under N2
6. 6
   기타Approximately 2 hours later, the starting material is consumed
7. 7
   온도The reaction is cooled
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    workup.DISSOLUTIONthe residue is dissolved in ethyl acetate
11. 11
    세척washed with H2O, brine
12. 12
    건조dried (Na2SO4)
13. 13
    여과filtered
14. 14
    농축concentrated
15. 15
    기타is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)

실험 절차

In a 2 L flask, 2-bromo-4,6-difluoro-N-carbethoxy aniline (42 g, 150 mmol) in CH3CN (500 mL) is degassed with vacuum and purged with N2. Dichlorobis(triphenylphosphine)palladium(II) (10.5 g, 15 mmol, 10 mol %), followed by CuI (710 mg, 4 mmol, 2.5 mol %) and triethyl amine (41 mL) are added and rinsed in with 100 mL of CH3CN. Trimethylsilyl acetylene (31.8 ml, 225 mmol) is added and reaction is refluxed under N2. Approximately 2 hours later, the starting material is consumed, indicated by TLC (20% ethyl acetate/hexane, UV). The reaction is cooled, filtered, concentrated, and the residue is dissolved in ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, concentrated, and is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient) to yield 30 g of 2-(trimethylsilylethynyl)-4,6-difluoro-N-carbethoxyaniline (71%).

출처