Trimethylsilyl cyanide → HCID 53403951, Verbindung

HRID 336825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336825
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12])=[O:4].C[Si]([C:17]#[N:18])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.[Cl-].[Na+]>[F:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 223137872-Bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone

Produkt 1

HCID 53403951HCID 53403951, VerbindungAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5234Sodium ChlorideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2.5 g (10.73 mmol) of 2-bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone in 100 ml of acetonitrile are respectively added 1.2 g (11.8 mmol) of trimethylsilyl cyanide and 12.3 ml (12.3 mmol) of tetrabutyl-ammonium fluoride solution (1M in THF). The reaction mixture is stirred at room temperature for 16 h then diluted with an aqueous solution saturated with sodium chloride. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered, then evaporated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5) to give 1.2 g (62%) of 3-(2-fluoro-4-hydroxyphenyl)-3-oxopropanenitrile in the form of a yellow solid.

Aufarbeitung

  1. extractionThe product is extracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5)

Quellen und Nachweise

ORD-Eintrag
ord-1eb2817b5b214bbdb5573717dbb5971b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889711B2

Notizen zur Reaktion

Wird geladen…