Water → Ethyl (4-bromo-2,6-dimethylphenoxy)acetate

HRID 2220630

Reaction equation

HRID 2220630 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([CH3:17])[CH:10]=1.C([O-])(=O)C.[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:16][C:12]1[C:13]([CH3:15])=[CH:14][C:9]([Br:8])=[CH:10][C:11]=1[CH3:17])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 169194-Bromo-2,6-dimethylphenolHCID 517044Potassium Acetate

Product 1

HCID 875019Ethyl (4-bromo-2,6-dimethylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl bromoacetate (0.662 mL) was added to a mixture of 4-bromo-2,6-dimethylphenol (1.0 g) and potassium acetate (1.031 g) in N,N-dimethylformamide (10 mL), and the mixture was stirred at 80° C. for 3 hrs. 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: ethyl acetate/n-hexane=1/10) to afford the title compound (1.29 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: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-25ea414057584b038524dd258874c7e8
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Linked notes

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