Water → Clofibrate

HRID 2247315Notes

Reaction equation

HRID 2247315 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:7][CH2:6][O:5][C:3]([C:2]([O:17][C:14]1[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=1)([CH3:9])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 2796Clofibrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 2-bromo-2-methyl-propanoate and p-chlorophenol was dissolved in dry acetone and treated with potassium carbonate. After stirring at rt for 30 min., the mixture was refluxed for 16 h. The reaction mixture was poured into water and extracted with DCM. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica, hexanes:EtOAc, 9:1, 6:1 to 3:1) to give the desired product, which was used in the following step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica, hexanes:EtOAc, 9:1, 6:1 to 3:1)

Sources & evidence

ORD record
ord-88d48834bfb047d0867bf571c841f2df
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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