Water → HCID 57809581, Verbindung

HRID 2106413

Reaktionsgleichung

Reaktionsgleichung von HRID 2106413
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=1)[CH:31]=[O:32].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:31]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:32])[CH:33]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 57809595((4-Bromophenyl)ethynyl)triisopropylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 57809581HCID 57809581, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phase are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1).

Aufarbeitung

  1. additionare added dropwise over 15 min
  2. waitThe resulting solution is left in the cooling bath
  3. temperatureto warm up overnight to ambient temperature
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe combined organic phase are dried over sodium sulphate
  6. customthe solvent is removed
  7. customThe residue is purified through silica gel (cyclohexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-0cdab6fdac004177b7a929c51952fbf4
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579449B2

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