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Potassium Carbonate → HCID 86698652, Verbindung

HRID 338305
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 338305
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CCO.C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([CH3:10])[CH:9]=2)=[CH:18][CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57736551HCID 57736551, Verbindung

Produkt 1

HCID 86698652HCID 86698652, VerbindungAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 702EthanolLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-bromo-4-methyl-5-nitro-benzonitrile (522.0 mg, 2.17 mmol), 4-methoxyphenyl boronic acid (329.0 mg, 2.17 mmol) and 2N aqueous potassium carbonate (6.56 mL, 13.1 mmol) in EtOH (6 mL) and toluene (3 mL) was degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed with N2 for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 3 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was filtered and the solids were air dried to give the title compound (145 mg). The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (25-75% EtOAc/heptane) to give the title compound (337 mg). The two lots of the title compound were combined (482 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.78 (s, 1H), 7.63 (d, J=8.78 Hz, 2H), 7.14 (d, J=8.59 Hz, 2H), 3.85 (s, 3H), 2.64 (s, 3H).

Aufarbeitung

  1. customwas degassed with N2 for 5 minutes
  2. customdegassed with N2 for an additional 5 minutes
  3. customThe reaction mixture was sealed
  4. temperatureThe reaction was cooled to room temperature
  5. customthe layers were separated
  6. filtrationThe organic layer was filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6fdfd8a305864dfdaf435e34d2f45bd7
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889730B2

Notizen zur Reaktion

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