Water → HCID 59824992, compound

HRID 886588Notes

Reaction equation

HRID 886588 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)=[O:6])[CH3:2].[CH3:15][Mg]Br.O>CCOCC>[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)([OH:6])[CH3:15])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 12252915ethyl 2-(3-bromophenyl)-2-oxoacetateHCID 178418573HCID 178418573, compound

Product 1

HCID 59824992HCID 59824992, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (2.5 g, 9.8 mmol) in ether (20 mL) at 0° C. was added methyl magnesium bromide (10.8 mmol, 3 M in ether, 3.6 mL) with stirring. The reaction was stirred at 0° C. for 15 min. Water was added and the crude partitioned between ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane to afford 2-(3-bromo-phenyl)-2-hydroxy-propionic acid ethyl ester as a colorless liquid. (1.87 g, 70% yield). MS: m/z 273 (M+H+).

Workup

  1. stirringThe reaction was stirred at 0° C. for 15 min
  2. customthe crude partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-45f4caf38bc04484a1ae83c3a79a724e
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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