Dichlorodimethylsilane → 4-Chlorodimethylsilylbenzonitrile

HRID 247632

Reaktionsgleichung

[C:1]([C:3]1[CH:11]=[CH:10][C:6](C(Cl)=O)=[CH:5][CH:4]=1)#[N:2].Cl[Si:13]([CH3:19])([CH3:18])[Si](C)(C)Cl.[C]=O.C[Si](C)(Cl)[Cl:24]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:24][C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[C:4]([SiH:13]([CH3:19])[CH3:18])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

A reaction mixture containing 10 gm (6×10-2 mole) of p-cyanobenzoyl chloride and 15 gm (1.25 mole equivalent) of 1,2-dichlorotetramethyldisilane was heated to 135° C. during which time the solution became homogeneous. A cocatalyst mixture containing 200 mg. bis(benzonitrile)palladiumdichloride (1 mole %) and 274 mg triphenylphosphine (2 mole %) was then introduced. Carbon monoxide gas evolution began immediately and the reaction was heated at 140° C. for 12 hours while dimethyldichlorosilane was continuously removed. Vacuum distillation gave 7 gm (60% isolated yield) of 4-chlorodimethylsilylbenzonitrile, bp. 93°/0.1 torr, m.p. 40°-43° C. The resulting chlorodimethylsilylbenzonitrile, in the form of a low melting high moisture sensitive solid was hydrolyzed to the corresponding 1,3-bis(4'-benzonitrile)tetramethyldisiloxane in the form of a colorless liquid. The identity of the disiloxane was further confirmed by its NMR and IR spectra.

Aufarbeitung

additionA cocatalyst mixture containing 200 mg
customwas continuously removed
distillationVacuum distillation

Quellen und Nachweise

ORD-Eintrag: ord-cb6a7eabdcee432a8f29787889f303d6
Quelldatensatz: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04709054

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