Water → HCID 67059819, Verbindung

HRID 601448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601448
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N+:18]([C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)([O-:20])=[O:19].O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Komponenten

7

Edukt 3

HCID 962WaterHCID 124951-Iodo-4-nitrobenzeneHCID 4197992(4-octylphenyl)boronic Acid

Produkt 1

HCID 67059819HCID 67059819, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0) (0.30 g, 0.26 mmol) and p-n-octylphenylboronic acid (1.0 g, 4.3 mmol) were sequentially added to a stirred solution of 4-nitroiodobenzene (0.87 g, 3.5 mmol) in 1,2-dimethoxyethane (13 mL) and aqueous sodium carbonate (2 M, 13 mL) under dry nitrogen. The stirred mixture was heated under reflux overnight and cooled. Water was added and the product was extracted into ether (30 3 mL) and the combined ethereal extracts were washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by chromatography using a short silica gel column (hexane:ethyl acetate—5:1 to 2:1] to provide 4′-nitro-4-n-octyl-biphenyl as a yellow oil, which solidified upon standing (1.04 g, 95% yield). The solid was used without further purification.

Aufarbeitung

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. extractionthe product was extracted into ether (30 3 mL)
  5. washthe combined ethereal extracts were washed with brine
  6. dry with materialdried with MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e49c8341712a4098bdb96ce32e9bfe59
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902363B2

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