Potassium Carbonate → N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

HRID 2063184

Reaktionsgleichung

Reaktionsgleichung von HRID 2063184
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.B(O)(O)[C:16]1[CH:21]=[CH:20][C:19]([N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C>[C:4]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:32]3[CH:33]=[CH:34][C:29]([N:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:19]4[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=4)=[CH:30][CH:31]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 64257864-BromodiphenylamineHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 22013295N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4.3 g (17 mmol) of 4-bromodiphenylamine, 5 g (17 mmol) of triphenylamine-4-boronic acid, and 532 mg of tri(o-tolyl)phosphine were put into a 500 mL three-neck flask, and the atmosphere in the flask was substituted by nitrogen. 60 mL of toluene, 40 mL of ethanol, and 14 ml of a potassium carbonate aqueous solution (0.2 mol/L) were added into this mixture. The mixture was deaerated while being stirred under reduced pressure, and after deaeration, 75 mg (0.35 mmol) of palladium(II) acetate was added. This mixture was refluxed at 100° C. for 10.5 hours. An aqueous layer of the mixture was extracted with toluene. The extracted solution and an organic layer were washed together with saturated brine, and magnesium sulfate was added thereto for drying. This mixture was filtrated and the filtrate was concentrated to obtain an oily light-brown substance. The oily substance was dissolved in about 50 mL of toluene, and was subjected to suction filtration through Celite (manufactured by Celite Co., Ltd.), alumina, and Florisil (manufactured by Floridin Company). A solid substance obtained by concentrating the filtrate was purified by a silica gel column chromatography (developing solvent was a mixed solvent of hexane:toluene=4:6) to obtain a white solid substance. The obtained white solid substance was recrystallized with chloroform/hexane, so that 3.5 g of an white substance was obtained in yield 49%.

Aufarbeitung

  1. extractionAn aqueous layer of the mixture was extracted with toluene
  2. washThe extracted solution and an organic layer were washed together with saturated brine, and magnesium sulfate
  3. additionwas added
  4. customfor drying
  5. filtrationThis mixture was filtrated
  6. concentrationthe filtrate was concentrated
  7. customto obtain an oily light-brown substance
  8. filtrationwas subjected to suction filtration through Celite (manufactured by Celite Co., Ltd.), alumina, and Florisil (manufactured by Floridin Company)
  9. customA solid substance obtained
  10. concentrationby concentrating the filtrate
  11. customwas purified by a silica gel column chromatography (
  12. customtoluene=4:6) to obtain a white solid substance
  13. customThe obtained white solid substance was recrystallized with chloroform/hexane, so that 3.5 g of an white substance
  14. customwas obtained in yield 49%

Quellen und Nachweise

ORD-Eintrag
ord-1f3dc9feaddc4004872e685823702b92
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288012B2

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