Chlorotrimethylsilane → Benzonitrile, 3-fluoro-6-methyl-2-(trimethylsilyl)-

HRID 1107716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107716
C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:15]=[C:16]([C:19]([CH3:22])=[CH:20][CH:21]=1)[C:17]#[N:18].[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>C1COCC1>[F:13][C:14]1[C:15]([Si:24]([CH3:26])([CH3:25])[CH3:23])=[C:16]([C:19]([CH3:22])=[CH:20][CH:21]=1)[C:17]#[N:18]

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 5226685-Fluoro-2-methylbenzonitrileHCID 178418339Butyllithium

Produkt 1

HCID 18785863Benzonitrile, 3-fluoro-6-methyl-2-(trimethylsilyl)-Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (1.40M in hexanes, 11.8 mmol, 8.44 ml) was added dropwise to a stirred solution of diisopropylamine (1.84 ml) in THF (5 ml) at 0° C. After 30 min., the solution was cooled to -78° C. and 3-fluoro-6-methylbenzonitrile (1.60 g, 11.8 mmol) in THF (5 ml) was added dropwise. The pale purple anion was stirred for 20 min., trimethylsilylchoride (3.0 ml, 24 mmol) was added and the mixture warmed to room temperature over 1 h, evaporated, the residue taken up in a small amount of diethyl ether and filtered. Evaporation of the filtrate gave an off-white crystalline solid (2.3 g), m.p. 71-73° C.

Aufarbeitung

  1. temperaturethe mixture warmed to room temperature over 1 h
  2. customevaporated
  3. filtrationfiltered
  4. customEvaporation of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-25934cccc74b468aa9553b38ef4ba855
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063789

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