Monoperoxyphthalic Acid Magnesium Salt → 4-Fluoro-1-methylsulfinyl-2-nitrobenzene

HRID 1452928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452928
C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:5].[Mg+2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1>CO.ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:23])=[O:5])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1

Komponenten

5

Edukt 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 127009114-Fluoro-1-(methylsulfanyl)-2-nitrobenzene

Produkt 1

HCID 225673464-Fluoro-1-methylsulfinyl-2-nitrobenzeneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-Fluoro-1-methylsulfinyl-2-nitrobenzene can be obtained in the following way: 4.7 g of magnesium monoperoxyphthalate are added portionwise to a solution, under argon, of 1.9 g of 4-fluoro-1-methylsulfanyl-2-nitrobenzene in 6 ml of methanol and 30 ml of dichloromethane. The reaction mixture is then stirred at a temperature in the region of 20° C. for 3 hours, and is then filtered through sintered glass and the solid is washed with dichloromethane. The filtrate is washed with an aqueous sodium hydrogencarbonate solution then with water, dried over magnesium sulfate, treated with 3S black, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue thus obtained is purified by chromatography on a column of 125 g of silica (particle size 40-63 μm), eluting with pure dichloromethane. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.3 g of 4-fluoro-1-methylsulfinyl-2-nitrobenzene are thus obtained in the form of a yellow foam (Rf=0.23, silica gel thin layer chromatography, eluent: dichloromethane/ethyl acetate 90/10)).

Aufarbeitung

  1. filtrationis then filtered through sintered glass
  2. washthe solid is washed with dichloromethane
  3. washThe filtrate is washed with an aqueous sodium hydrogencarbonate solution
  4. dry with materialwith water, dried over magnesium sulfate
  5. additiontreated with 3S black
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe residue thus obtained
  9. customis purified by chromatography on a column of 125 g of silica (particle size 40-63 μm)
  10. washeluting with pure dichloromethane
  11. additionThe fractions containing the expected product
  12. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-8484ef0709fd4c8ba4684f628059ec6b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473701B2

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