Water → 3-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

HRID 397151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397151
[N:1](OCCCC)=[O:2].[CH3:8][C:9]1[C:14]([CH3:15])=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:11][C:10]=1[Br:20].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[Br:20][C:10]1[C:9]([CH3:8])=[C:14]([C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=1)[CH:15]=[N:1][OH:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10996Butyl nitriteHCID 187572522,3-Dimethyl-4-methylsulfonylbromobenzeneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 734619443-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 2.1 g (20 mmol) of n-butyl nitrite (97%) and 4 g (15 mmol) of 2,3-dimethyl-4-methylsulfonylbromobenzene in 50 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 2.8 g (25 mmol) of potassium tert-butoxide in 35 ml of dimethylformamide is added dropwise at this temperature, over a period of 20 minutes. The reaction is monitored by HPLC. For work-up, initially 10 ml of water are added, and the mixture is then adjusted to pH 5-6 using about 9 ml of glacial acetic acid. The mixture is then poured onto 100 ml of ice-water and the aqueous phase is extracted with methylene chloride. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. This gives 3.6 g of an oily crude product (90% by HPLC) which can be purified by recrystallization from toluene.

Aufarbeitung

  1. extractionthe aqueous phase is extracted with methylene chloride
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives 3.6 g of an oily crude product (90% by HPLC) which can be purified by recrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-a83e75c0c9354d4bb531f2579eeee50b
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608209B2

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