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Sodium Carbonate → 4-(5-Methoxy-3-pyridinyl)benzonitrile

HRID 1685403
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1685403
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)#[N:11].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O.CO.C1(C)C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)[CH:3]=[N:4][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 8171633-Bromo-5-methoxypyridineHCID 27343264-Cyanophenylboronic acid

Produkt 1

HCID 672914774-(5-Methoxy-3-pyridinyl)benzonitrileAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.93 g (10.3 mM) of 3-bromo-5-methoxypyridine and 1.85 g (12.36 mM) of 4-cyanophenylboronic acid are mixed with 40 ml of toluene and 40 ml of methanol. 0.6 g (0.5 mM) of tetrakis(triphenylphosphine)palladium and 1.3 g (30.9 mM) of lithium chloride are added. 26 ml of 1 M sodium carbonate solution are then added. The mixture is refluxed for 5 hours and, after cooling, water and ethyl acetate are added to the reaction medium. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and then concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (94/6; v/v) as the eluent to give the expected product in the form of a beige solid with a yield of 89%.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureafter cooling
  3. customThe aqueous phase is separated off
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (94/6; v/v) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6fe4c18ad00544e98a7a30d0911a6d3c
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148407B2

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