Hexane → (2-Methoxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane

HRID 2263450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263450
[CH3:1][O:2][C:3]1[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][C:6]([CH3:13])=[CH:5][C:4]=1Br.CCCCCC.C([Li])CCC.[CH2:26]([Si:28]([CH2:31]C)(Cl)[Cl:29])C>C(OCC)C>[CH3:1][O:2][C:3]1[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][C:6]([CH3:13])=[CH:5][C:4]=1[Si:28]([Cl:29])([CH3:31])[CH3:26]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 15589DiethyldichlorosilaneHCID 6178701-Bromo-3-tert-butyl-2-methoxy-5-methylbenzeneHCID 178418339Butyllithium

Produkt 1

HCID 11032947(2-Methoxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, 2-methoxy-1-bromo-3-tert-butyl-5-methylbenzene (20.00 g, 77.77 mmol) was dissolved in 200 mL of diethyl ether. A 1.57 M hexane solution of n-butyllithium (59.44 mL, 93.32 mmol) was dropwise added at −50° C. or lower, and a temperature was raised to room temperature, followed by stirring for 1 hour. All the amount of diethyldichlorosilane (24.44 g, 155.54 mmol) was added to the mixture at once at −50° C. or lower, and a temperature was gradually raised to room temperature. After being refluxed for 1 hour, the solution was concentrated under reduced pressure. Hexane was added, the insolubles were filtered off with a Celite filter, and the filtrate was concentrated under reduced pressure. Concentration was further continued at 70° C. under reduced pressure for 3 hours to obtain (2-methoxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane. Resultant (2-methoxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane was used in a subsequent reaction without further purification.

Aufarbeitung

  1. temperaturelower, and a temperature was gradually raised to room temperature
  2. temperatureAfter being refluxed for 1 hour
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionHexane was added
  5. filtrationthe insolubles were filtered off with a Celite
  6. filtrationfilter
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. concentrationConcentration
  9. waitwas further continued at 70° C. under reduced pressure for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-46884fa744ed402e90d94afd22542e10
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851569B2

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