Cesium carbonate → 4-Chloro-2-[4-(methylsulfonyl)-2-(trifluoromethyl)phenoxy]-benzeneacetic acid

HRID 910873Notes

Reaction equation

HRID 910873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([OH:12])[CH:3]=1.F[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=1[C:24]([F:27])([F:26])[F:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([O:12][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][C:15]=2[C:24]([F:25])([F:27])[F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1338254-Chloro-2-hydroxyphenylacetic acidHCID 534159651-Fluoro-4-(methylsulfonyl)-2-(trifluoromethyl)benzene

Product 1

HCID 116256724-Chloro-2-[4-(methylsulfonyl)-2-(trifluoromethyl)phenoxy]-benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the product from step (ii) (0.125 g), the product of example 44 step (i) (0.150 g) and cesium carbonate (0.437 g) in NMP (10 ml) was stirred at 80° C. for 10 h. The mixture was partitioned between 2M sodium hydroxide and diethyl ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate and the organic layer dried and evaporated under reduced pressure. The residue was purified using RP prep HPLC. Yield 0.025 g.

Workup

  1. customThe mixture was partitioned between 2M sodium hydroxide and diethyl ether
  2. extractionextracted with ethyl acetate
  3. customthe organic layer dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-ed87fbfb457e4e4b9e105f54e1fec991
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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