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Toluene → HCID 57823325, Verbindung

HRID 2352746
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2352746
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>[Pd].O.C(O)C>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 232384604-Bromo-4'-ethyl-1,1'-biphenyl

Produkt 1

HCID 57823325HCID 57823325, VerbindungAusbeute 145,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938
Palladium
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5.6 g (21.4 mmol) of 4-bromo-4′-ethylbiphenyl, 3.6 g (25.7 mmol) of 3-fluorophenyl dihydroxyborane, 4.4 g (32.2 mmol) of potassium carbonate, 0.3 g of 5%-Pd/C and 60 mL of a mixed solvent of toluene, ethanol and water (ratio: 1/1/1) was refluxed for 6 hours to obtain a reaction solution. After removing the catalyst by filtration, 50 mL of toluene was added to the reaction solution, which was then washed with water. The reaction solution having been washed with water was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the reaction solution under reduced pressure to obtain 8.6 g of a residue. The residue was purified by silica gel column chromatography (eluent: heptane/toluene=4/1) to obtain 5.1 g of crude crystals of the compound (E-8). The crude crystals were dissolved in a mixed solvent of ethanol and ethyl acetate (ratio: 10/1) and recrystallized therefrom to obtain 4.5 g of purified crystals of the compound (E-8).

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. customto obtain a reaction solution
  3. customAfter removing the catalyst
  4. filtrationby filtration, 50 mL of toluene
  5. additionwas added to the reaction solution, which
  6. washwas then washed with water
  7. washThe reaction solution having been washed with water
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off from the reaction solution under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c130930e19648e8a0ef1061eacc59b4
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07749403B2

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