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Trimethyl borate → HCID 86654468, Verbindung

HRID 878855
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 878855
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.COB(OC)OC.Br[C:21]([C:23]([F:26])([F:25])[F:24])=[CH2:22].C(=O)([O-])[O-].[K+].[K+]>CCCCCC.C([Li])CCC.O1CCCC1.O.C(OC)(C)(C)C>[Cl:8][C:6]1[CH:7]=[C:2]([C:21]([C:23]([F:26])([F:25])[F:24])=[CH2:22])[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 8470Trimethyl borateHCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 202698551-Bromo-3-chloro-5-(trifluoromethyl)benzene

Produkt 1

HCID 86654468HCID 86654468, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8058HexaneLösungsmittel
HCID 15413tert-Butyl methyl etherLösungsmittel
HCID 178418339ButyllithiumLösungsmittel

Versuchsvorschrift

In a solution of 2.60 g of 3-bromo-5-chlorobenzotrifluoride and 1.2 mL of tert-butylmethyl ether in 25 mL of hexane, 6.38 mL of n-butyl lithium (1.6M hexane solution) was added dropwise at −10° C. with stirring, and stirred at the same temperature for 30 minutes. Then, a solution of 1.09 g of trimethoxyborane in 10 mL of tetrahydrofuran was added dropwise. After the completion of the addition dropwise, it was stirred at the same temperature further for 10 minutes and then the temperature was raised to room temperature. Then, in the reaction mixture, 2.60 g of 2-bromo-3,3,3-trifluoropropene, 2.76 g of potassium carbonate, 15 mL of water and 0.0065 g of 1,3-bis(2,6-diisopropylphenyl)imidazole-2-ilidene (1,4-naphthoquinone) palladium (0) dimmer were added, and stirred under nitrogen atmosphere at 60° C. for 6 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off, and the organic phase was collected and the aqueous phase was extracted with 30 mL of ethyl acetate twice.

Aufarbeitung

  1. stirringstirred at the same temperature for 30 minutes
  2. additionAfter the completion of the addition dropwise
  3. stirringit was stirred at the same temperature further for 10 minutes
  4. stirringstirred under nitrogen atmosphere at 60° C. for 6 hours
  5. customAfter the completion of the reaction
  6. waitthe reaction mixture was left
  7. temperaturecooled to room temperature
  8. filtrationinsoluble material was filtered off
  9. customthe organic phase was collected
  10. extractionthe aqueous phase was extracted with 30 mL of ethyl acetate twice

Quellen und Nachweise

ORD-Eintrag
ord-d9efd0649ad740fbaa4cf14486739830
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987464B2

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