Water → HCID 22118244, Verbindung

HRID 2080054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080054
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.C(OCC)(=O)C.O.[CH3:22][N:23](C)C=O>[C-]#N.[Zn+2].[C-]#N.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>[O:4]([C:5]1[N:6]=[C:7]([C:22]#[N:23])[CH:8]=[CH:9][CH:10]=1)[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:2]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 131696982-(2-bromophenoxy)pyridine

Produkt 1

HCID 22118244HCID 22118244, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Next, to a solution of the resulting 2-bromo-phenoxy-pyridine (1.0 g, 4.0 mmol) in N,N-dimethylformamide (30 mL) were added zinc cyanide (940 mg, 8.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (924 mg, 0.8 mmol) under nitrogen atmosphere, and the mixture was stirred at 100° C. for 1 hour. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and 6-phenoxy-pyridine-2-carbonitrile (524 mg, 67%) was obtained as a white solid.

Aufarbeitung

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-83813633426a40cfb510322c57a2380f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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