Reaktion #688630

Reaktionsgleichung

p-n-octylphenylboronic acid

4-nitroiodobenzene

Water

→

4′-nitro-4-n-octyl-biphenyl

Ausbeute 95.0%

Lösungsmittel

1,2-dimethoxyethane

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe stirred mixture was heated
2. 2
   Temperaturunder reflux overnight
3. 3
   Temperaturcooled
4. 4
   Extraktionthe product was extracted into ether (30 3 mL)
5. 5
   Waschenthe combined ethereal extracts were washed with brine
6. 6
   Trocknendried with MgSO4
7. 7
   SonstigeThe solvent was removed in vacuo
8. 8
   Sonstigethe residue was purified by chromatography

Vorschrift

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.

Quelle