Sodium Bicarbonate → [[4'-(Methylsulfonyl)-2',5-bis(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetic acid, 1,1-dimethylethyl ester

HRID 1694760Notes

Reaction equation

HRID 1694760 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=2[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:5]([C:28]([F:31])([F:30])[F:29])[CH:4]=1.[C:32](=O)(O)[O-].[Na+].O[O:38][S:39]([O-:41])=O.[K+]>CC(C)=O.O>[CH3:32][S:39]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][C:10]=2[O:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[C:5]([C:28]([F:29])([F:30])[F:31])[CH:4]=1)(=[O:41])=[O:38]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 86609223[[4'-(Methylthio)-2',5-bis(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetic acid, 1,1-dimethylethyl ester

Product 1

HCID 86609224[[4'-(Methylsulfonyl)-2',5-bis(trifluoromethyl)[1,1'-biphenyl]-2-yl]oxy]acetic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The product from step (iv) (0.564 g) was dissolved in 50% aqueous acetone (10 ml), sodium bicarbonate (0.94 g) added, followed by a solution of oxone (1.5 g) in water (ml) and stirred for 3 h. The reaction was quenched with aqueous sodium metabisulfite, extracted with EtOAc, washed with aqueous potassium carbonate, dried (Na2SO4) and evaporated to give the subtitle compound. Yield 0.32 g.

Workup

  1. customThe reaction was quenched with aqueous sodium metabisulfite
  2. extractionextracted with EtOAc
  3. washwashed with aqueous potassium carbonate
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c6e7c1cd1d924347922cfe85419fc3ec
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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