Chlorotrimethylsilane → (6-Bromo-2,3-difluorophenyl)trimethylsilane

HRID 34020

Reaktionsgleichung

Reaktionsgleichung von HRID 34020
C(NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[Br:13][C:14]1[C:15]([Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([F:21])[C:17]([F:20])=[CH:18][CH:19]=1

Komponenten

9

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 676754-Bromo-1,2-difluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 23070109(6-Bromo-2,3-difluorophenyl)trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under nitrogen atmosphere, to a solution of 18.2 mL of N,N-diisopropylamine in 200 mL of tetrahydrofuran was added 66.0 mL of 1.57 M n-butyllithium in hexane at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 20.0 g of 1-bromo-3,4-difluorobenzene in 100 mL of tetrahydrofuran was added dropwise and stirred at this temperature for 30 minutes, stirred at this temperature for 30 minutes, added dropwise with 32.9 mL of chlorotrimethylsilane, and the reaction solution was allowed to warm gradually to room temperature, and stirred for a day. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane)-, to afford 20.3 g of the title compound as a colorless oil.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringstirred at this temperature for 30 minutes
  3. stirringstirred at this temperature for 30 minutes
  4. temperatureto warm gradually to room temperature
  5. stirringstirred for a day
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified
  10. customseparated by silica gel column chromatography (n-hexane)-

Quellen und Nachweise

ORD-Eintrag
ord-895884dedeb242c3b6988f0654c0ede9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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