p-Fluoronitrobenzene → 3,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole

HRID 527520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527520
[CH3:1][C:2]1[C:6]2=[C:7]([OH:12])[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]2[O:4][N:3]=1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1363786503,6-Dimethyl-1,2-benzisoxazol-4-ol2×

Produkt 1

HCID 679598393,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazoleAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3,6-dimethyl-1,2-benzisoxazol-4-ol (Intermediate 19, 345 mg) was dissolved in acetonitrile (10.0 ml) and then 1-fluoro-4-nitrobenzene (298 mg, 2.11 mmol) and potassium carbonate (877 mg, 6.34 mmol) were added. The reaction mixture was stirred and heated at reflux overnight. After removal of the volatiles, the residue was purified by silica gel chromatography eluting with a gradient cHex/EtOAc from 100/0 to 50/50 to afford the title compound (208 mg).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customAfter removal of the volatiles
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with a gradient cHex/EtOAc from 100/0 to 50/50

Quellen und Nachweise

ORD-Eintrag
ord-f9283790676b454eab2e3e83a0ddffd1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346790B2

Notizen zur Reaktion

Wird geladen…