Toluene → HCID 59492609, Verbindung

Temperatur

110 °C

To a reaction vessel were added 1-bromo-2-chloro-4-fluorobenzene (25 g), ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (46 g), toluene (125 ml), water (125 ml) and tripotassium phosphate (50.5 g), and purged with argon. To this mixture was added dichlorobis(triphenylphosphine)palladium(II) (1.67 g) and the mixture was stirred in an oil bath at 110° C. for 3 hr. The oil bath was removed, and water (125 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hr, and filtered through celite. The filtrate was partitioned in a separatory funnel. The aqueous layer was extracted with toluene, and the organic layers were combined. The organic layer was washed twice with water (125 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (41.8 g). The obtained solid was directly used for the next reaction without further purification.

1. custompurged with argon
2. additionTo this mixture was added dichlorobis(triphenylphosphine)palladium(II) (1.67 g)
3. customThe oil bath was removed
4. additionwater (125 ml) was added to the reaction mixture
5. stirringThe mixture was stirred at room temperature for 1 hr
6. filtrationfiltered through celite
7. customThe filtrate was partitioned in a separatory funnel
8. extractionThe aqueous layer was extracted with toluene
9. washThe organic layer was washed twice with water (125 ml)
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-c97f15e3c5ff41308520743859458a71

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08871934B2