Toluene → HCID 71238684, Verbindung

HRID 1502193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502193
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1>C(O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:3][CH:4]=3

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 534010773,6-Dibromo-9-(4-methylphenyl)-9H-carbazole

Produkt 1

HCID 71238684HCID 71238684, VerbindungAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3,6-Dibromo-N-(4-methylphenyl)carbazole (6.23 g) and phenylboronic acid (2.01 g) were added to a solvent mixture of toluene (60 mL) and ethanol (15 mL), followed by bubbling with nitrogen. Then, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture, and the resultant mixture was refluxed under nitrogen flow for 5 hours. The mixture was diluted with toluene. The toluene layer was washed with water and dried and the toluene was evaporated. The residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass)), to thereby obtain 3.20 g of 3-bromo-6-phenyl-N-(4-methylphenyl)carbazole as colorless powder.

Aufarbeitung

  1. customby bubbling with nitrogen
  2. additionThen, tetrakistriphenylphosphine palladium (290 mg) and 21.2% aqueous sodium carbonate solution (15.0 g) were added to the mixture
  3. temperaturethe resultant mixture was refluxed under nitrogen flow for 5 hours
  4. additionThe mixture was diluted with toluene
  5. washThe toluene layer was washed with water
  6. customdried
  7. customthe toluene was evaporated
  8. additionThe residue was treated through silica gel column chromatography (eluent: toluene/hexane=1/4 (by mass))

Quellen und Nachweise

ORD-Eintrag
ord-575baa2aace94c44ad6a14d54e804c2f
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206202B2

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