反应详情

温度

60 °C

To a stirred solution of 4-bromo-2-chlorobenzoic acid, methyl ester (18.69 g) in triethylamine (110 ml), was added 1-dimethylamino-2-propyne (12.1 ml), bis(triphenylphosphine)palladium(II) chloride (1.26 g), and copper(I) iodide (0.136 g). The mixture was heated slowly to 60° C., and the temperature maintained for one hour. The reaction was cooled to room temperature, filtered through diatomaceous earth, and the collected solid washed with ethyl acetate. The solvent was removed in vacuo, the resulting residue redissolved in ethyl acetate, and washed with water (3×). The combined organic extract was dried over anhydrous sodium sulfate, and the solvent removed in vacuo to give a crude product. The crude product was purified by column chromatography on silica gel (225 g), eluting with 40% ethyl acetate/hexane. After removing the solvent in vacuo, the title compound was obtained as a viscous oil (17.7 g), MS (+FAB), m/z: 252 (M+H)+.

1. temperaturethe temperature maintained for one hour
2. temperatureThe reaction was cooled to room temperature
3. filtrationfiltered through diatomaceous earth
4. washthe collected solid washed with ethyl acetate
5. customThe solvent was removed in vacuo
6. dissolutionthe resulting residue redissolved in ethyl acetate
7. washwashed with water (3×)
8. extractionThe combined organic extract
9. dry with materialwas dried over anhydrous sodium sulfate
10. customthe solvent removed in vacuo
11. customto give a crude product
12. customThe crude product was purified by column chromatography on silica gel (225 g)
13. washeluting with 40% ethyl acetate/hexane
14. customAfter removing the solvent in vacuo