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Toluene → 2,5-Dimethyl-4'-hexyloxybiphenyl

HRID 1635761
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1635761
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.[CH2:23]([O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 11430Potassium CarbonateHCID 36821484-Hexyloxyphenylboronic Acid

Produkt 1

HCID 186766192,5-Dimethyl-4'-hexyloxybiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Bromo-p-xylene (8.3 g, 45 mmol) (cf. A1 a)), K2CO3 (12.4 g, 90 mmol), 70 ml of toluene and 70 ml of H2O were placed in a reaction vessel and argon was passed in for 30 minutes. 4-hexyloxyphenylboronic acid (10 g, 45 mmol) and Pd(PPh3)4 (0.65 g, 0.56 mmol) were subsequently added under protective gas. The yellow-green, turbid mixture was stirred vigorously under a blanket of protective gas for about 20 hours at an internal temperature of 85° C. After phase separation, the organic phase was shaken with dilute HCl/H2O (until neutral). The aqueous phase was shaken with toluene and the organic phases were combined. After filtering off any palladium residues, the solution was evaporated. The crude product was purified by distillation under reduced pressure: the product was obtained as a yellow oil (boiling point: 117°-125° C./0.08 mbar): 10.3 g (81%). Purity>95% (1H-NMR).

Aufarbeitung

  1. customwas passed in for 30 minutes
  2. customAfter phase separation
  3. stirringthe organic phase was shaken with dilute HCl/H2O (until neutral)
  4. stirringThe aqueous phase was shaken with toluene
  5. filtrationAfter filtering off any palladium residues
  6. customthe solution was evaporated
  7. distillationThe crude product was purified by distillation under reduced pressure
  8. customthe product was obtained as a yellow oil (boiling point: 117°-125° C./0.08 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-28d132ad7a944018b7dc1ca657b3b54a
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06509507B2

Notizen zur Reaktion

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