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

HRID 2243530Notes

Reaction equation

HRID 2243530 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)C.[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:11]([O:16][CH2:17][CH3:18])[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 517044Potassium AcetateHCID 218775414-Bromo-2-ethoxyphenol

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl bromoacetate (1.04 mL) was added to a mixture of 4-bromo-2-ethoxyphenol (1.69 g) and potassium acetate (1.62 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 an hydrous 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 an hydrous 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-2d60b6e67c0b40debaf248cd94298832
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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