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

HRID 1675625
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1675625
[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]
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Komponenten

9

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d11ad3a22bcb4cb2baa36a337829d142
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003703B2

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