Water → 1,2,4-Trifluoro-5-methanesulfinyl-benzene

HRID 2066854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066854
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[C:17]([S:19][CH3:20])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[OH2:23]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])=[O:9])[C:16]([F:21])=[CH:15][C:14]=1[F:22].[F:12][C:13]1[CH:18]=[C:17]([S:19]([CH3:20])(=[O:9])=[O:23])[C:16]([F:21])=[CH:15][C:14]=1[F:22]

Komponenten

7

Edukt 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 467394612,4,5-Trifluorothioanisole

Produkt 2

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneAusbeute 14 %HCID 673085031,2,4-Trifluoro-5-methanesulfinyl-benzeneAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

MCPBA (4.93 g, 22 mmol) in DCM (20 mL) was added to an ice cooled solution of 43a (22 mmol) in DCM (40 mL). After 2 h, the mixture was diluted with water (30 mL) and saturated NaHCO3 (30 mL) and stirred for 20 minutes. The organic layer was removed and the aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were dried and concentrated. The residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane) to afford 1,2,4-trifluoro-5-methanesulfinyl-benzene 43b (0.41 g, 24% yield, HPLC, LC-MS 195.0 (MH)) and 1,2,4-trifluoro-5-methanesulfonyl-benzene 43c (0.63 g, 14%) as white powders.

Aufarbeitung

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash LC(10 to 40% EtOAc+0.1% triethylamine in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7bcaf7230a314be98cb59779fd5f5fe0
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293729B2

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