반응 #70662

반응 방정식

2,7-dibromofluorene

sodium hydroxide

3-(4-bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene

→

9-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

용매

DMSO

반응 조건

후처리

1. 1
   기타the reaction was quenched by the addition of DI water (10 mL)
2. 2
   기타The excess salt was removed by filtration
3. 3
   workup.ADDITION500 mL Ethyl acetate was added
4. 4
   추출extracted with DI water (3×300 mL) and brine (3×300 mL)
5. 5
   건조The combined organic layer was dried over anhydrous magnesium sulfate
6. 6
   기타Magnesium sulfate was removed by filtration
7. 7
   기타the solvent was removed by rotary evaporation
8. 8
   기타The product (43 g) was purified by flash chromatography

실험 절차

To an oven-dried three-neck round-bottom flask under nitrogen, were added 25.97 g of 2,7-dibromofluorene, 32.06 g sodium hydroxide, 1.33 g KI, and 300 mL anhydrous DMSO. The 46 g 3-(4-bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene 300 mL anhydrous DMSO was added via cannula. The reaction was heated to 80° C. After 4 hours, the reaction was quenched by the addition of DI water (10 mL). The excess salt was removed by filtration. 500 mL Ethyl acetate was added, and extracted with DI water (3×300 mL) and brine (3×300 mL). The combined organic layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the solvent was removed by rotary evaporation. The product (43 g) was purified by flash chromatography using hexane. The structure was confirmed by NMR.

출처