反应详情

A mixture of p-fluoroacetanilide (76.5 g, 0.5 mole), 4-bromofluorobenzene (262.5 g, 1.5 mole), K2CO3 (76 g, 0.55 mole), Cu2Br2 (157.8 g, 0.55 mole) and N-methylpyrrolidone (600 ml) were heated at 175°-180°. After allowing low boiling material to condense off, the mixture was heated at reflux for 7 days. The mixture was cooled to 60° and quenched into a mixture of 2 liters H2O, 600 ml ethylenediamine and 1.2 liters toluene, filtered and the toluene layer separated, back-washed 2×600 ml H2O, treated with activated carbon, dried over MgSO4 and concentrated to oily solids in vacuo. The latter were taken up in 1.5 liters 10% ethanolic KOH, refluxed 18 hours and concentrated in vacuo to an oil. The oil was partitioned between 750 ml H2O and 750 ml. ether. The water layer was washed 2× 200 ml ether. The organic layers were combined, back-washed 2×200 ml H2O, treated with activated carbon, dried over MgSO4, reconcentrated to an oil (60.3 g) and distilled to yield purified title product 41.6 g, b.p. 158°-160°/2 mm.

1. temperaturewere heated at 175°-180°
2. customto condense off, the mixture
3. temperaturewas heated
4. temperatureat reflux for 7 days
5. temperatureThe mixture was cooled to 60°
6. customquenched into a mixture of 2 liters H2O, 600 ml ethylenediamine and 1.2 liters toluene
7. filtrationfiltered
8. customthe toluene layer separated
9. washback-washed 2×600 ml H2O
10. additiontreated with activated carbon
11. dry with materialdried over MgSO4
12. concentrationconcentrated to oily solids in vacuo
13. temperaturerefluxed 18 hours
14. concentrationconcentrated in vacuo to an oil
15. customThe oil was partitioned between 750 ml H2O and 750 ml
16. washThe water layer was washed 2× 200 ml ether
17. washback-washed 2×200 ml H2O
18. additiontreated with activated carbon
19. dry with materialdried over MgSO4
20. distillationdistilled
21. customto yield
22. custompurified title product 41.6 g, b.p. 158°-160°/2 mm