Toluene → HCID 59492872, Verbindung

HRID 541131

Reaktionsgleichung

Reaktionsgleichung von HRID 541131
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].CC1(C)C(C)(C)OB([C:18]2[CH:28]=[CH:27][CH:26]=[CH:25][C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])O1.C1(C)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:3]([CH3:9])[CH:4]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 844762-Bromo-5-chlorotolueneHCID 2773962Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Produkt 1

HCID 59492872HCID 59492872, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, a mixture of 2-bromo-5-chloro-toluene (20.55 g), ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (55.23 g), toluene (200 ml), water (125 ml), tripotassium phosphate (53.07 g) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (1.633 g) was stirred with heating under reflux for 1 hr. The reaction mixture was cooled to room temperature, activated carbon (1 g) was added and the mixture was stirred for 10 min at room temperature. The insoluble material was filtered off, and the filtrate was partitioned in a separatory funnel. The organic layer was washed twice with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=98/2) to give the title compound (27.20 g, 99%).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. additionactivated carbon (1 g) was added
  4. stirringthe mixture was stirred for 10 min at room temperature
  5. filtrationThe insoluble material was filtered off
  6. customthe filtrate was partitioned in a separatory funnel
  7. washThe organic layer was washed twice with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=98/2)

Quellen und Nachweise

ORD-Eintrag
ord-5f997e45d3144a3488a2ca99c79c64fc
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871934B2

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