反应详情

温度

55 °C

To a solution of 2-bromofluorobenzene (49 g), 1-dodecyne (210 ml) triethylamine (210 ml), and tetrahydrofuran (50 ml) was added (bis)triphenylphosphine palladium(II)chloride (532 mg) and copper(I)iodide (532 mg). The reaction mixture was warmed to 55° C. and stirred for 24 hr. The mixture was allowed to cool to room temperature and filtered. The precipitate was washed with ethyl acetate, and the filtrate was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with hexane). The appropriate fractions were collected and evaporated. The residue was distilled to afford 11 g (15%) of product, bp 175°-180° C. at 1 mm Hg.

1. temperatureto cool to room temperature
2. filtrationfiltered
3. washThe precipitate was washed with ethyl acetate
4. additionthe filtrate was diluted with ethyl acetate
5. washwashed with water and brine
6. customThe organic phase was separated
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated in vacuo
10. customchromatographed over silica gel (eluted with hexane)
11. customThe appropriate fractions were collected
12. customevaporated
13. distillationThe residue was distilled