Iodine → tert-Butyldiphenylchlorosilane

HRID 1274508

Reaktionsgleichung

Reaktionsgleichung von HRID 1274508
[Mg].II.[C:4](Cl)([CH3:7])([CH3:6])[CH3:5].C([Mg]Cl)(C)(C)C.[C:15]1([Si:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(Cl)[Cl:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu].COCCOC>[C:4]([Si:21]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[Cl:22])([CH3:7])([CH3:6])[CH3:5]

Komponenten

8

Edukt 5

HCID 807IodineHCID 6627DichlorodiphenylsilaneHCID 10486tert-BUTYL CHLORIDEHCID 5462224MagnesiumHCID 178418310HCID 178418310, Verbindung

Produkt 1

HCID 94078tert-ButyldiphenylchlorosilaneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

48.6 g (2.0 mol) of magnesium filings and a spatula-tip of iodine are initially introduced into a 2 1 three-necked flask with a precision glass stirrer, straight enclosed-scale thermometer, Dimroth condenser and dropping funnel under a blanket of inert gas. By addition of 600 ml of ethylene glycol dimethyl ether and 203.7 g (2.2 mol) of tert-butyl chloride, tert-butylmagnesium chloride is prepared. Initially 5.2 g (0.02 mol) of copper(II) acetylacetonate and then, at 50° C. over 2 hours, 455.8 g (1.8 mol) of diphenyldichlorosilane are subsequently added dropwise. The internal temperature of the flask rises slightly, and the mixture is subsequently stirred at 70° C. for a further 3 hours to bring the reaction to completion. To remove the precipitated magnesium salt from the solution, the reaction mixture is filtered through a pressure suction filter maintained under an argon atmosphere. The filter cake is rinsed with ethylene glycol dimethyl ether. A concluding fractional distillation of the combined filtrates in vacuo gives 420.6 g of tert-butyldiphenylchlorosilane (85% yield, based on the diphenyldichlorosilane) as a colorless liquid in a GC purity of 92%.

Aufarbeitung

  1. customis prepared
  2. customthe reaction to completion
  3. customTo remove the precipitated magnesium salt from the solution
  4. filtrationthe reaction mixture is filtered through a pressure suction
  5. filtrationfilter
  6. temperaturemaintained under an argon atmosphere
  7. washThe filter cake is rinsed with ethylene glycol dimethyl ether
  8. distillationA concluding fractional distillation of the combined filtrates in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cbde98aec9034104afcedb1ef2902e1d
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156918

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