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

HRID 2243532

Reaction equation

HRID 2243532 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>[Br:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:11]([CH3:17])[CH:10]=1

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 (0.66 mL) was added to a mixture of 4-bromo-2,6-dimethylphenol (1.0 g) and potassium acetate (1.03 g) in N,N-dimethylformamide (10 mL), and 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 (elent: 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 (elent: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-9fd5853b2c01415ba37b4c30914cfe81
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Linked notes

Loading…