2-Bromophenol → 4-(2-Bromophenoxy)butyric acid ethyl ester

HRID 2081309Notes

Reaction equation

HRID 2081309 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15]Br)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:9]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH3:10]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 150701144-(2-Bromophenoxy)butyric acid ethyl esterYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.65 g of bromophenol and 8.75 g of 4-bromobutyric acid ethyl ester are dissolved in 120 ml of dimethylformamide, mixed with 32.6 g of cesium carbonate and stirred for 2 days at room temperature. The reaction mixture is filtered, the solvent is distilled off in a vacuum and the residue is distilled in a bulb tube at 180° C./0.4 mbar. 11 g of 4-(2-bromophenoxy)butyric acid ethyl ester is obtained as a colorless oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationthe solvent is distilled off in a vacuum
  3. distillationthe residue is distilled in a bulb tube at 180° C./0.4 mbar

Sources & evidence

ORD record
ord-502ccf6aea974a858717eeda5255c69c
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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