Triphenylarsine → 4-Acetylbiphenyl

HRID 368917

Reaktionsgleichung

Reaktionsgleichung von HRID 368917
O([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)S(C(F)(F)F)(=O)=O.[C:18]1([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+].[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN1C(=O)CCC1>[C:18]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 5

HCID 11773TriphenylarsineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 607632TributylphenyltinHCID 27693554-Acetylphenyl Trifluoromethanesulfonate

Produkt 1

HCID 71134-AcetylbiphenylAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Table 1, Entry 11. In the reaction tube were mixed 4-acetylphenyl triflate (0.268 g, 1.0 mmol), phenyltributyltin (0.441 g, 1.2 mmol), Pd2 dba3 (0.00916 g, 0.010 mmol), triphenylarsine (0.0245 g, 0.080 mmol), lithium chloride (0.127 g, 3.0 mmol) and 1.0 ml NMP.under nitrogen. The contents of the flask were irradiated for 2.50 min with an effect of 50 W. After cooling, addition of 1 M aqueous KF (4 ml) with stirring for 120 min, were followed by dilution (DCM) and filtration through a pad of celite. The filtrate was washed with water (25 ml). Additional extraction of the aqueous phase was performed with DCM (2×25 ml). The combined extracts were washed with 25 ml saline and concentrated to an oil. The crude product was purified by column chromatography on silica gel using i-hexane/ethyl acetate (10/1) as the eluent. The yield was 68% (white solid).

Aufarbeitung

  1. customThe contents of the flask were irradiated for 2.50 min with an effect of 50 W
  2. temperatureAfter cooling
  3. filtrationwere followed by dilution (DCM) and filtration through a pad of celite
  4. washThe filtrate was washed with water (25 ml)
  5. extractionAdditional extraction of the aqueous phase
  6. washThe combined extracts were washed with 25 ml saline
  7. concentrationconcentrated to an oil
  8. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7947dcb83ce145efbc8e93dbce181aff
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136157

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