Réaction #1340561

Équation de réaction

Na2CO3

toluene

→

o-terphenyl

Rendement 40.0%

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is heated up
2. 2
   Températureto reflux under nitrogen
3. 3
   TempératureThe reaction mixture is heated
4. 4
   Températureunder reflux for 6 hours
5. 5
   Températurecooled
6. 6
   Autrethe phases formed
7. 7
   Autreare separated
8. 8
   Extractionthe water phase is extracted with dichloromethane
9. 9
   Autredried
10. 10
    AutreThe solvent is removed under reduced pressure
11. 11
    Autrethe crude product is purified by means of a short silica gel column
12. 12
    AutreAfter purification by column chromatography (dichloromethane/hexane, 2:1)

Mode opératoire

6.4 mmol of the dibromide (VI) and 6.4 mmol of the arylboronic acid derivative (V) (2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)pyridine) are dissolved in 25 ml of toluene. 0.4 mmol of Pd(PPh3)4 and 10 ml of a 4N solution of Na2CO3 are added, and the mixture is heated up to reflux under nitrogen. The reaction mixture is heated under reflux for 6 hours and cooled, the phases formed are separated, and the water phase is extracted with dichloromethane and dried. The solvent is removed under reduced pressure and the crude product is purified by means of a short silica gel column. After purification by column chromatography (dichloromethane/hexane, 2:1), the desired o-terphenyl derivative is obtained in from 40 to 50% yield.

Source