Chlorotrimethylsilane → (4-Bromo-3,5-dimethylphenyl)trimethylsilane

HRID 237482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237482
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:10].C([Li])CCC.Cl[Si:17]([CH3:20])([CH3:19])[CH3:18]>C(OCC)C.O1CCCC1.CCCCCC>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][C:3]=1[CH3:10]

Komponenten

7

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 27580472,5-Dibromo-1,3-dimethylbenzeneHCID 178418339Butyllithium

Produkt 1

HCID 86697146(4-Bromo-3,5-dimethylphenyl)trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 2,5-dibromo-1,3-dimethylbenzene (500 mg) in diethylether (3 mL) and tetrahydrofuran (2.5 mL) is cooled to −78° C. and treated dropwise with n-butyllithium (200 μL of a 10 M solution in n-hexane). The mixture is stirred for 1 hour and treated dropwise with chloro-trimethyl-silane (275 μL). After stirring for 2 hours the reaction is quenched by addition of saturated aqueous NH4Cl solution. The mixture is extracted with diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→90:10) to give the title compound. Yield: 260 mg; Mass spectrum (ESI+): m/z=279 [M+Na]+.

Aufarbeitung

  1. stirringAfter stirring for 2 hours the reaction
  2. customis quenched by addition of saturated aqueous NH4Cl solution
  3. extractionThe mixture is extracted with diethylether
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→90:10)

Quellen und Nachweise

ORD-Eintrag
ord-e10e31b119794a4995336d41bc01d136
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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