Dichlorodimethylsilane → 4-Chlorodimethylsilylbenzonitrile

HRID 247632

반응식

HRID 247632 반응식
[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

참가 물질

7

반응물 4

HCID 6398DichlorodimethylsilaneHCID 780451,2-Dichloro-1,1,2,2-tetramethyldisilaneHCID 801724-Cyanobenzoyl chlorideHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 1317153954-Chlorodimethylsilylbenzonitrile수율 60%

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 498840Bis(benzonitrile)palladium chloride촉매

반응 조건

온도
135 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-cb6a7eabdcee432a8f29787889f303d6
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709054

연결된 노트

불러오는 중…