Dichlorodimethylsilane → 4-Chlorodimethylsilylbenzonitrile

HRID 247632

反応式

HRID 247632 の反応式
[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

参加物

7

反応物 4

HCID 6398DichlorodimethylsilaneHCID 780451,2-Dichloro-1,1,2,2-tetramethyldisilaneHCID 801724-Cyanobenzoyl chlorideHCID 178418416HCID 178418416、化合物

生成物 1

HCID 1317153954-Chlorodimethylsilylbenzonitrile収率 60%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 498840Bis(benzonitrile)palladium chloride触媒

反応条件

温度
135 °C

実験手順

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.

後処理

  1. additionA cocatalyst mixture containing 200 mg
  2. customwas continuously removed
  3. distillationVacuum distillation

出典と根拠

ORDレコード
ord-cb6a7eabdcee432a8f29787889f303d6
出典データセット
uspto-grants-1987_11
特許番号
US04709054

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