1-[2-(Benzyloxy)ethoxy]-4-(2-bromoethyl)benzene → 2-[4-(2-Bromoethyl)phenoxy]ethanol

HRID 916793Notes

Reaction equation

HRID 916793 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][Br:20])=[CH:14][CH:13]=1)C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[Br:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 689408411-[2-(Benzyloxy)ethoxy]-4-(2-bromoethyl)benzene

Product 1

HCID 693843602-[4-(2-Bromoethyl)phenoxy]ethanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(benzyloxy)ethoxy]-4-(2-bromoethyl)benzene in EtOAc (150 mL) and EtOH (50 mL) was hydrogenated over 10% Pd/C (530 mg) at room temperature and atmospheric pressure for 8 h. The catalyst was removed by filtration over Celite, washed with EtOAc and concentrated in vacuo to give the title compound (3.6 g). LCMS RT=2.82 min.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc5a031a0e4543a8a902e51c9fdb3279
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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