Ethyl bromoacetate → HCID 69484347, compound

HRID 1374073Notes

Reaction equation

HRID 1374073 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-:14].[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:14][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 78066(+-)-Methyl mandelate

Product 1

HCID 69484347HCID 69484347, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g (60.2 mmol) of hydroxyphenylacetic acid methyl ester (Aldrich) is dissolved in 75 ml of acetone. 18.4 g (133 mmol) of solid potassium carbonate is added. 17.8 ml (123 mmol) of bromoacetic acid ethyl ester is added in drops under reflux within 15 minutes, it is kept at this temperature for another 4 hours, and it is stirred overnight at room temperature. Precipitate is filtered out, the solution is evaporated to the dry state and chromatographed on silica gel (hexane/ethyl acetate 3:1). The fractions that contain the product are combined and concentrated by evaporation.

Workup

  1. temperatureunder reflux within 15 minutes
  2. filtrationPrecipitate is filtered out
  3. customthe solution is evaporated to the dry state
  4. customchromatographed on silica gel (hexane/ethyl acetate 3:1)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0d6af63761b64020b80493e8fd05a3c9
Source dataset
uspto-grants-2007_01
Patent number
US07164016B2

Reaction notes

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