Reacción #75456

Ecuación de reacción

4,4′-diiodobiphenyl

3,5-di-α-naphthyl bromobenzene

magnesium

1,2-dibromoethane

→

solid

Rendimiento 81.0%

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

Rendimiento 81.0%

Disolventes

THF

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturathe brown solution was heated
3. 3
   Temperaturaat reflux for 2 hrs
4. 4
   Temperaturaand then cooled to room temperature
5. 5
   workup.ADDITIONwas then added
6. 6
   Otroan orange solution resulted
7. 7
   TemperaturaHeat
8. 8
   TemperaturaThe mixture was then heated
9. 9
   Temperaturaat reflux for 45 min.
10. 10
    Temperaturacooled to room temperature during which time a solid
11. 11
    Otroprecipitated out of solution
12. 12
    workup.ADDITIONA 2.0 M solution of HCl was added to the mixture
13. 13
    Otrothe water layer was removed
14. 14
    FiltraciónThe solid precipitate was collected by filtration
15. 15
    Lavadowashed with water and diethyl ether

Procedimiento

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%)

Fuente