Hydrochloric Acid → 2,3-Difluoro-6-nitro-(2-p-toluenesulfonyloxypropyl)oxybenzene

HRID 846335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846335
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:14]([OH:16])[CH3:15].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:14]([O:16][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH3:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 146971862,3-Difluoro-6-nitro-[(2-hydroxypropyl)oxy]benzene

Produkt 1

HCID 146971942,3-Difluoro-6-nitro-(2-p-toluenesulfonyloxypropyl)oxybenzeneAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 4.5 g of the compound obtained in Example 5 in 8.6 ml of pyridine was added 4.36 g of p-toluenesulfonyl chloride and the mixture was stirred under cooling with ice for 4 hours, and then at room temperature for 4 hours. To the mixture were added ethyl acetate and 1 N hydrochloric acid. The mixture was shaken, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography to yield 6.52 g of the titled compound.

Aufarbeitung

  1. temperatureunder cooling with ice for 4 hours
  2. stirringThe mixture was shaken
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9befeeaef754feabada5e183d0022f7
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05136059

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