تفاعل #1548071

معادلة التفاعل

4-iodoanisole

4-bromo-3-nitro acetophenone

hexane ethyl acetate

→

title compound

المردود 36.0%

4-Acetyl-4'-methoxy-2-nitro biphenyl

المردود 36.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىis placed in an oil bath
2. 2
   درجة الحرارةThe temperature is slowly raised to 110° C.
3. 3
   درجة الحرارةUpon cooling the mixture
4. 4
   ترشيحfiltered through a Celite pad
5. 5
   أخرىThe filtrate and washings are evaporated
6. 6
   أخرىchromatographed (on silica Merck 60
7. 7
   أخرىpreabsorbed in dichloromethane
8. 8
   غسيلeluted with 9:1 hexane-ethyl acetate
9. 9
   أخرىto remove the impurities and 8:2 hexane-ethyl acetate
10. 10
    أخرىto recover the main product)

الإجراء التجريبي

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 washings 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.).

المصدر