Reacción #75455

Ecuación de reacción

4-bromobiphenyl

iodine

hexabromobenzene

4-Bromobiphenyl

→

1,2,4,5-tetra-p-biphenylylbenzene

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a condenser, a nitrogen inlet, an additional funnel and a magnetic stirring bar
2. 2
   Otroplaced in an additional funnel
3. 3
   Otrowas placed in a 50° C.
4. 4
   workup.ADDITIONwas added dropwise to the reaction
5. 5
   workup.ADDITIONAfter addition
6. 6
   Otrothe brownish reaction
7. 7
   Temperaturawas heated
8. 8
   Temperaturaat reflux for another hour
9. 9
   workup.ADDITIONwas added dropwise from an additional funnel to the reaction
10. 10
    OtroThe reaction was quenched with ice and 8% hydrochloric acid
11. 11
    Extracciónextracted with 400 mL of methylene chloride
12. 12
    LavadoThe organic layer was washed with saturated sodium chloride solution
13. 13
    Secadodried over magnesium sulfate
14. 14
    OtroSolvent was evaporated
15. 15
    Lavadothe crude product was washed with hexane
16. 16
    Filtraciónfiltered
17. 17
    Otroto give pure product

Procedimiento

Dry Mg turnings (3.9 g, 0.16 mol) and 30 mL of anhydrous THF were added to a 1 L 3-necked round-bottomed flask equipped with a condenser, a nitrogen inlet, an additional funnel and a magnetic stirring bar. 4-Bromobiphenyl (37.2 g, 0.16 mol) was dissolved in 150 mL of THF and placed in an additional funnel. The reaction flask was placed in a 50° C. oil bath and one crystal of iodine was added. Once the reaction started 4-bromobiphenyl was added dropwise to the reaction. After addition, the brownish reaction was heated at reflux for another hour and then cooled to room temperature. A suspension of hexabromobenzene (11.0 g, 0.02 mol) in 150 mL of THF was added dropwise from an additional funnel to the reaction and the mixture was stirred at room temperature overnight. The reaction was quenched with ice and 8% hydrochloric acid and extracted with 400 mL of methylene chloride. The organic layer was washed with saturated sodium chloride solution and dried over magnesium sulfate. Solvent was evaporated and the crude product was washed with hexane and filtered to give pure product.

Fuente