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

HRID 1675625Notes

Reaction equation

HRID 1675625 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:25]=[C:24]([F:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([OH:21])=[O:20].ClC1C=C(S(C)(=O)=O)C=CC=1SC1C=C(F)C=CC=1O.COC(=O)CBr.[OH-].[Na+].Cl>CN(C=O)C.O.C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:11])=[O:12])[CH:7]=[CH:6][C:5]=1[S:14][C:15]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 60984Methyl bromoacetateHCID 669954912-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenolHCID 67346100(2-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenoxy)acetic acid Sodium hydride

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

(2-{[2-Chloro-4-(methylsulfonyl)phenyl]thio}-4-fluorophenoxy)acetic acid 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-d11ad3a22bcb4cb2baa36a337829d142
Source dataset
uspto-grants-2011_08
Patent number
US08003703B2

Reaction notes

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