Hydrochloric Acid → 2-Nitro-4-((trifluoromethyl)sulfonyl)phenol

HRID 1968974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968974
[OH-:1].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18].CO.Cl>O.C(Cl)Cl>[N+:17]([C:5]1[CH:6]=[C:7]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[CH:8]=[CH:9][C:4]=1[OH:1])([O-:19])=[O:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Produkt 1

HCID 50351872-Nitro-4-((trifluoromethyl)sulfonyl)phenolAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Sodium hydroxide (211 mg, 5.28 mmol) was added to a suspension of 1-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene (297 mg, 1.03 mmol) in H2O (5 mL) at rt, followed by methanol (0.5 mL) to solubilise the starting material, and the reaction was heated at 110° C. for 1 h. The mixture was allowed to cool to rt, diluted with H2O (10 mL) and neutralised with 5 M HCl. DCM was added, the 2 layers were partitioned and the aqueous layer was extracted with DCM (2×). The combined organics were dried (Na2SO4) and concentrated by rotary evaporation to give 2-nitro-4-[(trifluoromethyl)sulfonyl]phenol (D82, 70 mg, 25%) as a colourless oil.

Aufarbeitung

  1. temperatureto cool to rt
  2. customthe 2 layers were partitioned
  3. extractionthe aqueous layer was extracted with DCM (2×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1cb5ed129a424bb29431cd0f3f40041f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426443B2

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