반응 #75456

반응 방정식

4,4′-diiodobiphenyl

3,5-di-α-naphthyl bromobenzene

magnesium

1,2-dibromoethane

→

solid

수율 81.0%

3,3″,5,5″-tetra-naphthyl-p-quaterphenyl

수율 81.0%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도the brown solution was heated
3. 3
   온도at reflux for 2 hrs
4. 4
   온도and then cooled to room temperature
5. 5
   workup.ADDITIONwas then added
6. 6
   기타an orange solution resulted
7. 7
   온도Heat
8. 8
   온도The mixture was then heated
9. 9
   온도at reflux for 45 min.
10. 10
    온도cooled to room temperature during which time a solid
11. 11
    기타precipitated out of solution
12. 12
    workup.ADDITIONA 2.0 M solution of HCl was added to the mixture
13. 13
    기타the water layer was removed
14. 14
    여과The solid precipitate was collected by filtration
15. 15
    세척washed with water and diethyl ether

실험 절차

A solution of 3,5-di-α-naphthyl bromobenzene (10.0 g, 0.0244 mol) in anhydrous THF (70 mL) was added dropwise to magnesium turnings (0.59 g, 0.0244 mol) in 10 mL THF. The solution was heated at 60° C. during the addition and the reaction was initiated using 1,2-dibromoethane. After the addition was complete, the brown solution was heated at reflux for 2 hrs. and then cooled to room temperature. In a separate flask, 4,4′-diiodobiphenyl (3.3 g 0.008 mol) and 0.3 g of dichlorobis(triphenyl phosphine)palladium(II) were placed under nitrogen and 30 mL of anhydrous THF was added. The Grignard reagent prepared about THF solution was then added using needle-transfer and an orange solution resulted. Heat was applied and the solution turned to almost black. The mixture was then heated at reflux for 45 min. and cooled to room temperature during which time a solid precipitated out of solution. A 2.0 M solution of HCl was added to the mixture and after stirring for 30 minutes, the water layer was removed. The solid precipitate was collected by filtration and washed with water and diethyl ether to yield a white solid (5.3 g, 81%)

출처