1-Bromo-3-(4-methoxy-but-1-enyl)-benzene → 1-Bromo-3-(4-methoxybutyl)benzene

HRID 1809815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809815
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1>C1COCC1.[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1

Komponenten

4

Edukt 1

HCID 675423861-Bromo-3-(4-methoxy-but-1-enyl)-benzene

Produkt 1

HCID 574358961-Bromo-3-(4-methoxybutyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of the title B compound, 1-bromo-3-(4-methoxy-but-1-enyl)-benzene (1.8 g, 7.46 mmol) and Pd/c 5% (0.36 g) in THF (20 mL) is shaked under an hydrogen atmosphere. After completion of the reaction, the mixture is filtered through a pad of celite, the solvent is evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (hexane/EtOAc 98/2) to give the title compound as a yellow oil: MS 260.1, 261.9 [M+18]. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 6.45 min.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe mixture is filtered through a pad of celite
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue purified by flash chromatography on silica gel (hexane/EtOAc 98/2)

Quellen und Nachweise

ORD-Eintrag
ord-5520688658df423fb4c8e83ed0dce04d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362040B2

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