反应详情

温度

100 °C

A solution of 4-bromophenol (0.173 g) in 4 mL of 1-methyl-2-pyrrolidone under argon atmosphere was treated with 4-(trifluoromethoxy)iodobenzene (0.313 mL), 2,2,6,6-tetramethylheptane-3,5-dione (0.046 mL) and caesium carbonate (0.652 g). The slurry was degassed by bubbling argon for 15 min and copper(I) chloride (0.099 g) was added. The reaction mixture was degassed by bubbling argon for 15 min, then heated to 100° C. under argon for 5 h. The reaction mixture was cooled to room temperature and added dropwise to 30 mL of tert-butyl-methyl-ether. The slurry was filtered and the solids washed with tert-butyl-methyl-ether (3×20 mL). The combined filtrates were washed subsequently with 1N NaOH (50 mL), water (50 mL), 2N HCl (50 mL), 1N HCl (50 mL), water (50 mL) and brine (50 mL). The resulting organic layer was dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel eluting with hexane to afford 0.15 g of the title compound as a colourless liquid.

1. customThe slurry was degassed
2. customby bubbling argon for 15 min
3. additioncopper(I) chloride (0.099 g) was added
4. customThe reaction mixture was degassed
5. customby bubbling argon for 15 min
6. temperatureThe reaction mixture was cooled to room temperature
7. additionadded dropwise to 30 mL of tert-butyl-methyl-ether
8. filtrationThe slurry was filtered
9. washthe solids washed with tert-butyl-methyl-ether (3×20 mL)
10. washThe combined filtrates were washed subsequently with 1N NaOH (50 mL), water (50 mL), 2N HCl (50 mL), 1N HCl (50 mL), water (50 mL) and brine (50 mL)
11. dry with materialThe resulting organic layer was dried over Na2SO4
12. concentrationconcentrated
13. customto give a crude product which
14. customwas purified by column chromatography on silica gel eluting with hexane