反应详情

温度

80 °C

A stirred mixture of 4-iodoanisole (43.65 g, 0.187 mole), 4-bromo-3-nitro acetophenone (40.6 g, 0.166 mole) and copper powder (copper bronze, 36 g, 0.567 mole) kept under nitrogen is placed in an oil bath heated at 80° C. The temperature is slowly raised to 110° C. and the mixture is kept at this temperature for 5 days (TLC, 8:2 hexane-ethyl acetate). Upon cooling the mixture is dissolved in dichloromethane and filtered through a Celite pad. The filtrate and washing are evaporated and the residual thick, dark brown oil (58.4 g) is flash chromatographed (on silica Merck 60, preabsorbed in dichloromethane, eluted with 9:1 hexane-ethyl acetate to remove the impurities and 8:2 hexane-ethyl acetate to recover the main product) to provide 16.2 g (32%) of the title compound (yellow solid, m.p.124°-126° C.).

1. customis placed in an oil bath
2. temperatureThe temperature is slowly raised to 110° C.
3. temperatureUpon cooling the mixture
4. filtrationfiltered through a Celite pad
5. washThe filtrate and washing
6. customare evaporated
7. customchromatographed (on silica Merck 60
8. custompreabsorbed in dichloromethane
9. washeluted with 9:1 hexane-ethyl acetate
10. customto remove the impurities and 8:2 hexane-ethyl acetate
11. customto recover the main product)