3-Nitrophenylboronic Acid → HCID 11615843, Verbindung

HRID 1059927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059927
Cl[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:6][C:4]([C:3]1[C:2]([C:19]2[CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=[CH:17][CH:18]=2)=[N:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Komponenten

7

Edukt 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 819931Methyl 2-chloronicotinate

Produkt 1

HCID 11615843HCID 11615843, VerbindungAusbeute 27,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of methyl 2-chloronicotinate (1.89 g), 3-nitrophenylboronic acid (1.67 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (11 ml). The mixture was stirred at 80° C. for 3 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was triturated with 2-propanol, filtered, washed with 2-propanol and dried under reduced pressure to give 3-(3-methoxycarbonylpyridin-2-yl)-nitrobenzene (713 mg).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with 2-propanol
  7. filtrationfiltered
  8. washwashed with 2-propanol
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18acd4eb5d57410c809d64ec696146ae
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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