Diethyl Malonate → Diethyl (4'-nitrobiphenyl-4-yl)malonate

HRID 1713859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713859
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]([O:31][CH2:32][CH3:33])=[O:30])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Komponenten

7

Edukt 3

HCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 2336104-Bromo-4'-nitro-1,1'-biphenyl

Produkt 1

HCID 59464037Diethyl (4'-nitrobiphenyl-4-yl)malonateAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-bromophenyl)nitrobenzene (Journal of Organic Chemistry, 2005, 70(9), 3730) (800 mg, 2.88 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (69 mg) and caesium carbonate (2.81 g, 8.63 mmol) in toluene (40 mL) was deoxygenated then palladium(II) acetate (13 mg, 0.06 mmol) and diethyl malonate (0.480 mL, 3.2 mmol) were added. The reaction mixture was heated under reflux for 2 h, cooled and then filtered through diatomaceous earth and the filter washed with EtOAc. The filtrate was concentrated by evaporation and adsorbed onto silica then purified by chromatography, eluting with 0-25% EtOAc in isohexane, to give the title compound (1.047 g) as a solid.

Aufarbeitung

  1. customwas deoxygenated
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 h
  4. temperaturecooled
  5. filtrationfiltered through diatomaceous earth
  6. washthe filter washed with EtOAc
  7. concentrationThe filtrate was concentrated by evaporation
  8. customthen purified by chromatography
  9. washeluting with 0-25% EtOAc in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-a552d6c04b8848d1983e7b9454fe2453
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795283B2

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