反应详情

A clean and dry 2000 ml round bottom flask equipped with reflux condenser, magnetic stir bar, and thermometer with adapter was prepared, purged, and then charged with 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophen-4,8-dione (7.34 g, 0.0333 mol). Anhydrous tetrahydrofuran (900.0 ml) was then added to this flask by cannula and stirring was initiated. Heat was applied to the reaction vessel to dissolve this material. The reaction vessel was placed into a water bath and m-tolylmagnesium bromide solution (100 ml, 0.1000 mol) was added via cannula. Following addition, the vessel was removed from the water bath and heated to reflux for 1 hour. The reaction was then removed from heat and allowed to cool to room temperature. m-tolylmagnesium bromide solution (100 ml, 0.1000 mol) was added via cannula and the reaction was again heated to reflux for 1 hour. The progress of the reaction was monitored by GC-MS and no starting material was present. The reaction was subsequently removed from heat and cool to room temperature overnight. A hydrochloric acid (160.0 ml, 10%)/tin (II) chloride (30.05 g, 0.1333 mol) solution was then prepared and added to the reaction via syringe. The reaction vessel was again heated to reflux for 1 hour, then removed from heat and allowed to cool to room temperature. Solvent was removed by rotary evaporation. Ethyl acetate (500.0 ml) was and the crude mixture was nearly dissolved. The volume was washed once with DI H2O (500 mL), and the organic layer containing solids was collected. Solids were removed by vacuum filtration, collected, and washed in hot methanol. The filtrate was dried over anhydrous magnesium sulfate, filtered, and removed of solvent by rotary evaporation. To the remaining crude material acetone (25.0 ml) and methanol (500.0 ml) were added and heated to reflux in trituration for 1 hour. The resulting solids in solution were vacuum-filtered and collected. All solids collected during purification were proved to be pure by NMR spectroscopy.

1. customA clean and dry 2000 ml round bottom flask
2. customequipped
3. temperaturewith reflux condenser, magnetic stir bar
4. customthermometer with adapter was prepared
5. custompurged
6. temperatureHeat
7. dissolutionto dissolve this material
8. customThe reaction vessel was placed into a water bath
9. additionaddition
10. customthe vessel was removed from the water bath
11. temperatureheated
12. temperatureto reflux for 1 hour
13. customThe reaction was then removed
14. temperaturefrom heat
15. temperaturethe reaction was again heated
16. temperatureto reflux for 1 hour
17. customThe reaction was subsequently removed
18. temperaturefrom heat
19. temperaturecool to room temperature overnight
20. additionadded to the reaction via syringe
21. temperatureThe reaction vessel was again heated
22. temperatureto reflux for 1 hour
23. customremoved
24. temperaturefrom heat
25. temperatureto cool to room temperature
26. customSolvent was removed by rotary evaporation
27. dissolutionthe crude mixture was nearly dissolved
28. washThe volume was washed once with DI H2O (500 mL)
29. additionthe organic layer containing solids
30. customwas collected
31. customSolids were removed by vacuum filtration
32. customcollected
33. washwashed in hot methanol
34. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
35. filtrationfiltered
36. customremoved of solvent by rotary evaporation
37. additionTo the remaining crude material acetone (25.0 ml) and methanol (500.0 ml) were added
38. temperatureheated
39. temperatureto reflux in trituration for 1 hour
40. filtrationThe resulting solids in solution were vacuum-filtered
41. customcollected
42. customAll solids collected during purification