Chlorosulfonic acid → 4-Methoxy-3-(trifluoromethyl)benzenesulfonyl chloride

HRID 2181870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181870
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[Cl:13][S:14](O)(=[O:16])=[O:15]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:5][C:4]=1[C:9]([F:10])([F:11])[F:12]

Komponenten

4

Edukt 2

HCID 24638Chlorosulfonic acidHCID 27752511-Methoxy-2-(trifluoromethyl)benzene

Produkt 1

HCID 224823844-Methoxy-3-(trifluoromethyl)benzenesulfonyl chlorideAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 1-methoxy-2-(trifluoromethyl)benzene (10.0 g, 56.8 mmol) in dry chloroform (76 mL) was cooled to 0° C. and treated with chlorosulfonic acid (7.55 mL, 113.5 mmol) drop-wise under argon. After the addition was completed, the reaction mixture was gradually warmed to room temperature and stirred overnight. The reaction was quenched by pouring the mixture slowly onto ice. The separated, aqueous phase was extracted with chloroform (3×). The combined organic phase was washed sequentially with a saturated, aqueous sodium chloride solution (2×) and water. The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound (8.77 g. 31.9 mmol, 56%) as a gray solid;

Aufarbeitung

  1. additionAfter the addition
  2. customThe reaction was quenched
  3. additionby pouring the mixture slowly onto ice
  4. extractionThe separated, aqueous phase was extracted with chloroform (3×)
  5. washThe combined organic phase was washed sequentially with a saturated, aqueous sodium chloride solution (2×) and water
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-454d07b0abb14def93e86a2a0fecf95b
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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