Water → Benzyl (4-bromo-2-isopropylphenoxy)acetate

HRID 30749

Reaction equation

HRID 30749 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[C:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 147934824-Bromo-2-(propan-2-yl)phenol

Product 1

HCID 85987904Benzyl (4-bromo-2-isopropylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromoacetate (0.88 mL) was added to a mixture of 4-bromo-2-isopropylphenol (1.0 g) and potassium carbonate (0.96 g) in N,N-dimethylformamide (5 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 benzyl (4-bromo-2-isopropylphenoxy)acetate (1.70 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-955170ffcdc14fa5b394e7627519e886
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Linked notes

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