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

HRID 2354972Notes

Reaction equation

HRID 2354972 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fafc85bb3d8b4a91948504fa903922d5
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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