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

HRID 2243528Notes

Reaction equation

HRID 2243528 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: diethylether/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: diethylether/n-hexane=1/10)

Sources & evidence

ORD record
ord-200fbf517440439baada4e65706be770
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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