Sodium Carbonate → 5-Chloro-3'-phenyl-2-methylbiphenyl

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%).

1. customTo a 2 L round bottle flask equipped
2. temperaturewith reflux condenser
3. customSolution was purged with nitrogen for 20 minutes
4. custompurged for another 10 minute
5. temperatureThe reaction was then heated under nitrogen for 18 hour
6. customAfter cooing to ambient temperature
7. customthe organic phase was separated
8. washwashed with 10% HCl (200 mL), water (200 mL) and saturated brine (200 mL)
9. dry with materialThis solution was dried with magnesium sulfate (50 g) for 3 hour
10. customthe solvent was removed by rotary evaporation
11. filtrationThe crude product was filtered
12. washwashing with hexane
13. additionProduct containing fractions
14. customcollected
15. customwere removed by Kruger-Rohr distillation

ORD-Eintrag

ord-289fa374ccec4861ae43e9f8f42b1f9b

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08648333B2