Reacción #328605

Ecuación de reacción

2-bromo-4-chlorotoluene

3-biphenylboronic acid

sodium carbonate

→

product

Rendimiento 77.0%

5-chloro-3′-phenyl-2-methylbiphenyl

Rendimiento 77.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 2 L round bottle flask equipped
2. 2
   Temperaturawith reflux condenser
3. 3
   OtroSolution was purged with nitrogen for 20 minutes
4. 4
   Otropurged for another 10 minute
5. 5
   TemperaturaThe reaction was then heated under nitrogen for 18 hour
6. 6
   OtroAfter cooing to ambient temperature
7. 7
   Otrothe organic phase was separated
8. 8
   Lavadowashed with 10% HCl (200 mL), water (200 mL) and saturated brine (200 mL)
9. 9
   SecadoThis solution was dried with magnesium sulfate (50 g) for 3 hour
10. 10
    Otrothe solvent was removed by rotary evaporation
11. 11
    FiltraciónThe crude product was filtered
12. 12
    Lavadowashing with hexane
13. 13
    workup.ADDITIONProduct containing fractions
14. 14
    Otrocollected
15. 15
    Otrowere removed by Kruger-Rohr distillation

Procedimiento

To a 2 L round bottle flask equipped with reflux condenser, stir bar, nitrogen feed, and oil bath were added 2-bromo-4-chlorotoluene (20.67 g, 98.59 mmol), 3-biphenylboronic acid (20.50 g 103.52 mmol), sodium carbonate (158 mL, 315 mmol), Aliquat 336 (4.00 g) and toluene (600 mL). Solution was purged with nitrogen for 20 minutes before adding tetrakis(triphenylphospine)palladium(0) (1.14 g, 0.98 mmol) and purged for another 10 minute. The reaction was then heated under nitrogen for 18 hour. After cooing to ambient temperature, the organic phase was separated, washed with 10% HCl (200 mL), water (200 mL) and saturated brine (200 mL). This solution was dried with magnesium sulfate (50 g) for 3 hour and the solvent was removed by rotary evaporation. The crude product was filtered, washing with hexane. Product containing fractions were identified by UPLC and collected. Low boiling point is impurities and solvents were removed by Kruger-Rohr distillation to give the product as colorless oil (20.2 g, 77%).

Fuente