Potassium Carbonate → Ethyl 2-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)acetate

HRID 1889189Notes

Reaction equation

HRID 1889189 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH:32]2[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(#N)C.C(OCC)(=O)C>[CH:32]1([S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH:17]([O:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH2:33][CH2:34]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 59610021Ethyl 2-bromo-2-(4-cyclopropylsulfonylphenyl)acetate

Product 1

HCID 59610052Ethyl 2-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluoro-phenoxy)acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-difluorophenol in acetonitrile, was added potassium carbonate followed by bromo-(4-cyclopropanesulfonyl-phenyl)-acetic acid ethyl ester (obtained in step I) and stirred for 10-14 hours. After completion, the reaction mixture was filtered; the filtrate was concentrated to obtain a residue which was dissolved in ethyl acetate; this solution was washed with water followed by brine solution, dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to provide a crude product which was purified by column chromatography to provide the compound A1-II.

Workup

  1. filtrationAfter completion, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto obtain a residue which
  4. washthis solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate, solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-356c81bf52ae46ecb180e382fbe8d902
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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