m-Chloroperbenzoic acid → 1-Nitro-3-[(propan-2-ylsulfonyl)methyl]benzene

HRID 514702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514702
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]SC(C)C)[CH:5]=1)([O-:3])=[O:2].Cl[C:16]1[CH:21]=CC=C(C(OO)=O)[CH:17]=1.[S:26]([O-:29])(O)=[O:27].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][S:26]([CH:16]([CH3:21])[CH3:17])(=[O:29])=[O:27])[CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 709764371-Nitro-3-[(propan-2-ylsulfanyl)methyl]benzene

Produkt 1

HCID 225020781-Nitro-3-[(propan-2-ylsulfonyl)methyl]benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-nitro-3-[(propan-2-ylsulfanyl)methyl]benzene (4.0 g) in DCM (160 mL) was treated at 0° C. with portions of m-chloroperbenzoic acid (9.3 g, 77%). The mixture was stirred at 0° C. for further 30 minutes and then 18 hours at room temperature. The reaction mixture was diluted with DCM before sodium hydrogen sulfite and sodium bicarbonate solution was added and extracted with DCM (2×). The combined organic phases were washed and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 12%-100%) to give the title compound (4.5 g).

Aufarbeitung

  1. custom18 hours
  2. customat room temperature
  3. additionwas added
  4. extractionextracted with DCM (2×)
  5. washThe combined organic phases were washed
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (hexane/ethyl acetate 12%-100%)

Quellen und Nachweise

ORD-Eintrag
ord-7b14bccc2ec14df88c74b110fb8359d7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108926B2

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