Phenol → Deschloroclofibrate

HRID 1890776Notes

Reaction equation

HRID 1890776 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:15][C:9]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 86476Deschloroclofibrate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of phenol (0.01 mol) and ethyl 2-bromo-2-methylpropanoate (0.01 mol) in acetonitrile was added Cs2CO3 (0.015 mol), and the reaction mixture was refluxed overnight. After removal of the solvent, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 1 N aqueous NaOH solution, water, and brine, and then dried sodium sulfate. Concentration gave the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.21˜7.25 (m, 2H), 6.98 (t, J=7.2 Hz 1H), 6.83˜6.86 (m, 2H), 4.23 (q, J=7.2 Hz 4H), 1.60 (s, 6H), 1.24 (t, J=7.2 Hz 3H); LCMS (ESI+) m/z 209 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customAfter removal of the solvent
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1 N aqueous NaOH solution, water, and brine
  5. concentrationConcentration

Sources & evidence

ORD record
ord-520ab8a5e7b947828ea13f4a9153d467
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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