Hydrochloric Acid → (2-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenoxy)acetic acid

HRID 1945221Notes

Reaction equation

HRID 1945221 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[S:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[OH:22].C[O:24][C:25](=[O:28])[CH2:26]Br.[OH-].[Na+].Cl>CN(C=O)C.O.C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[S:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[O:22][CH2:26][C:25]([OH:28])=[O:24]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 669954912-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenol

Product 1

HCID 11383734(2-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenoxy)acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% disp. oil, 0.024 g) was added to the product from step (iv) (0.20 g) in dry DMF (10 ml) and stirred at RT for 30 min before adding methyl-bromoacetate (0.060 ml). The solution was stirred at RT for 2 h, diluted with water and extracted with diethylether. The organics were dried and evaporated under reduced pressure to give an oil. The oil was dissolved in THF (20 ml) and water (10 ml) then sodium hydroxide (0.037 g) was added and stirred at RT overnight. The mixture was acidified with 2M HCl, extracted with ethyl acetate, the organics dried and evaporated under reduced pressure. The residue was purified by reverse phase HPLC. Yield 0.045 g

Workup

  1. stirringThe solution was stirred at RT for 2 h
  2. extractionextracted with diethylether
  3. customThe organics were dried
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. stirringstirred at RT overnight
  7. extractionextracted with ethyl acetate
  8. customthe organics dried
  9. customevaporated under reduced pressure
  10. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3b39a34bfe304438be7237c35de4a0f0
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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