Triethylamine → 3-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

HRID 2387707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2387707
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:9]=1)[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 27833303-Bromo-5-fluorobenzonitrile

Produkt 1

HCID 167372113-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A solution of 3-bromo-5-fluorobenzonitrile (2.5 g, 12.5 mmol), (trimethylsilyl)acetylene (2.86 ml, 20 mmol), bis(acetate)bis(triphenylphoshpino)Palladium(II) (936 mg, 1.25 mmol) and triethylamine (35 ml) in toluene (35 ml) was degassed by bubbling nitrogen through the solution and then stirred at 95° C. for 30 minutes. Filtration and concentration to yield a crude product. It was diluted with EtOAc (150 ml). The organic phase was washed with saturated NaHCO3 solution (50 ml), brine (50 ml) and the organic layer was dried over sodium sulfate. Filtration and concentration to yield a product A293.1 (2.4 g, 88%). HPLC: 95%, retention time: 4.05 minute (condition A). LC/MS (M+H)+=218.2.

Aufarbeitung

  1. customby bubbling nitrogen through the solution
  2. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-950a422e5b914f02bfe9e2318c5ee95f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268855B2

Notizen zur Reaktion

Wird geladen…