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Dimethylformamide → Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

HRID 1096951
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096951
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)(=O)=O.[CH3:25][N:26](C=O)C>[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>[C:25]([C:7]1[CH:8]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)#[N:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 57930914Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

Produkt 1

HCID 57346364Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Zinc cyanide (1.1 g) and Pd(PPh3)4 (281 mg) were added to a DMF (45 mL) solution of methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate (1.68 g), and stirred at 90° C. for 1 hour and 30 minutes. The reaction liquid was filtered through Celite, the solvent was partly evaporated away, and the residue was diluted with ethyl acetate, aqueous ammonia was added to it, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a white powder.

Aufarbeitung

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. customthe solvent was partly evaporated away
  4. additionthe residue was diluted with ethyl acetate, aqueous ammonia
  5. additionwas added to it
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-00e8522431594b2b8ce1b931a8ea608a
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138197B2

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