反应详情

In a 2L 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%).

1. custompurged with N2
2. additionare added
3. washrinsed in with 100 mL of CH3CN
4. customreaction
5. temperatureis refluxed under N2
6. customApproximately 2 hours later, the starting material is consumed
7. temperatureThe reaction is cooled
8. filtrationfiltered
9. concentrationconcentrated
10. dissolutionthe residue is dissolved in ethyl acetate
11. washwashed with H2O, brine
12. dry with materialdried (Na2SO4)
13. filtrationfiltered
14. concentrationconcentrated
15. customis purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)