反应详情

温度

175 °C

A mixture of 12 g (58.8 mmole) of N-acetyl-3,5-dichloroaniline, 8.13 g (58.8 mmole) of potassium carbonate (dried at 155° C. under vacuum), 23 g (147 mmole) of bromobenzene (dried over molecular sieves), and 1.12 g (5.9 mmole) of cuprous iodide was heated in a 175° C. oil bath under a reflux condenser under nitrogen for 18 hours. The mixture was cooled to room temperature and triturated with 1 liter of benzene. The solution was concentrated in vacuo. The residue was treated with 50 mL of EtOH and 7.76 g (118 mmole) of potassium hydroxide and the resulting mixture was heated to reflux for two hours. The mixture was cooled and the solvent removed in vacuo. The residue was taken up in 150 mL of hexanes and 20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 70 mL of water. The latter wash was back extracted with 60 mL of ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 200 g of silica gel with 2 liters of 50:1 hexanes:ethyl acetate to give 10 g (71%) of a yellow oil.

1. temperatureThe mixture was cooled to room temperature
2. customtriturated with 1 liter of benzene
3. concentrationThe solution was concentrated in vacuo
4. temperaturethe resulting mixture was heated
5. temperatureto reflux for two hours
6. temperatureThe mixture was cooled
7. customthe solvent removed in vacuo
8. wash20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 70 mL of water
9. washThe latter wash
10. extractionwas back extracted with 60 mL of ethyl acetate
11. dry with materialthe combined organic layers were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe residue was purified by flash chromatography on 200 g of silica gel with 2 liters of 50:1 hexanes