Potassium Carbonate → 2-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene

HRID 21474

Reaktionsgleichung

Reaktionsgleichung von HRID 21474
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=O)=O)=CC=1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 193744702-Fluoro-4-chloro-5-cyclopentyloxynitrobenzeneAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-4-chloro-5-hydroxynitrobenzene (7.1 g, 37.1 mmol) and potassium carbonate (5.1 g, 37.1 mmol) in acetonitrile (300 ml) was stirred for 2 hours at a refluxing temperature. Cyclopentyl p-toluenesulfonate (10.3 g, 40.8 mmol) was added thereto, followed by stirring further for 2 hours under refluxing. After completion of the reaction, the solvent was distilled off under reduced pressure from the reaction mixture, in hydrochloric acid (300 ml) was added thereto, and the mixture was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium bicarbonate and water, dried, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxynitrobenzene as a yellow solid (8.93 g, 34.3 mmol, 92.6% yield).

Aufarbeitung

  1. temperatureunder refluxing
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure from the reaction mixture, in hydrochloric acid (300 ml)
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (100 ml×3 times)
  6. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and water
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b1ea39f652a4ec0b1ad722b5587f73d
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424277

Verknüpfte Notizen

Wird geladen…