Reaction #1340561

Reaction equation

Na2CO3

toluene

→

o-terphenyl

Yield 40.0%

Conditions

Workup

1. 1
   Temperaturethe mixture is heated up
2. 2
   Temperatureto reflux under nitrogen
3. 3
   TemperatureThe reaction mixture is heated
4. 4
   Temperatureunder reflux for 6 hours
5. 5
   Temperaturecooled
6. 6
   Otherthe phases formed
7. 7
   Otherare separated
8. 8
   Extractionthe water phase is extracted with dichloromethane
9. 9
   Otherdried
10. 10
    OtherThe solvent is removed under reduced pressure
11. 11
    Otherthe crude product is purified by means of a short silica gel column
12. 12
    OtherAfter purification by column chromatography (dichloromethane/hexane, 2:1)

Procedure

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