反应详情

温度

95 °C

Commercially available 5-bromo-2-chloroanisole (1.0 g, 4.52 mmol), trimethylsilylacetylene (1.07 mL, 7.5 mmol) and triethylamine (15 mL) were added to anhydrous toluene (15 mL) and degassed by purging with nitrogen. Bis(acetato)bis(triphenylphosphine)palladium II (340 mg, 0.45 mmol) was added and the reaction mixture was heated to ˜95° C. for 30 min. The reaction mixture was cooled to room temperature, filtered to remove the catalyst, and diluted with ethyl acetate (150 mL). The organic layer was washed with saturated sodium bicarbonate (50 mL) and brine (50 mL) separated, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography over silica gel eluted with hexane/ethyl acetate 20:1 to yield A60.1 (807 mg, 75%). 1H NMR (400 MHz): δ 7.40-7.25 (m, 2H), 7.10-7.00 (m, 1H), 3.90, (s, 3H), 0.24 (s, 9H).

1. customdegassed
2. customby purging with nitrogen
3. temperatureThe reaction mixture was cooled to room temperature
4. filtrationfiltered
5. customto remove the catalyst
6. additiondiluted with ethyl acetate (150 mL)
7. washThe organic layer was washed with saturated sodium bicarbonate (50 mL) and brine (50 mL)
8. customseparated
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by flash column chromatography over silica gel
13. washeluted with hexane/ethyl acetate 20:1
14. customto yield A60.1 (807 mg, 75%)