反应详情

温度

120 °C

1-(4-bromo-5-chloro-2-hydroxyphenyl)ethanone (6.2 g, 25 mmol) was combined with zinc cyanide (4.4 g, 37 mmol) in N,N-dimethylformamide (40 mL) degassed with nitrogen and tris(dibenzylideneacetone)dipalladium(0) (0.38 g, 0.42 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.57 g, 0.99 mmol) were added. The reaction was degassed with nitrogen and heated to 120° C. and monitored by LC/MS. After heating for 2 hrs, the reaction was allowed to cool to room temperature, diluted with ethyl acetate, and filtered to remove the solids. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo to give the crude product. The product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-2-chloro-5-hydroxybenzonitrile as a yellow crystalline solid (3.5 g, 72%).

1. additionwere added
2. customThe reaction was degassed with nitrogen
3. temperatureAfter heating for 2 hrs
4. temperatureto cool to room temperature
5. additiondiluted with ethyl acetate
6. filtrationfiltered
7. customto remove the solids
8. washThe organic layer was washed with water, brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated in vacuo
11. customto give the crude product
12. customThe product was purified by FCC on silica gel
13. washeluting hexane