Water → Ethyl (4-bromo-2-ethoxyphenoxy)acetate

HRID 2220628Notes

Reaction equation

HRID 2220628 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH2:17][CH3:18])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:15][C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=1[O:16][CH2:17][CH3:18])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 218775414-Bromo-2-ethoxyphenol

Product 1

HCID 85987914Ethyl (4-bromo-2-ethoxyphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl bromoacetate (1.038 mL) was added to a mixture of 4-bromo-2-ethoxyphenol (1.694 g) and potassium carbonate (1.618 g) in N,N-dimethylformamide (10 mL), and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/10) to afford ethyl(4-bromo-2-ethoxyphenoxy)acetate (2.26 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/10)

Sources & evidence

ORD record
ord-9484e34bd65b4dbf91f391c2f449f7fc
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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