Potassium Carbonate → Methyl 2-nitro-5-[4-(trifluoromethyl)phenoxy]benzoate

HRID 1075316

Reaktionsgleichung

Reaktionsgleichung von HRID 1075316
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]1[CH:20]=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25]>CS(C)=O>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([O:1][C:19]2[CH:20]=[CH:21][C:22]([N+:29]([O-:31])=[O:30])=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 171018Methyl 5-chloro-2-nitrobenzoate

Produkt 1

HCID 13209694Methyl 2-nitro-5-[4-(trifluoromethyl)phenoxy]benzoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

p-Hydroxybenzotrifluoride (0.22 g, 1.36 mmol), powdered potassium carbonate (0.185 g, 1.34 mmol), and methyl 5-chloro-2-nitrobenzoate (0.288 g, 1.34 mmol) were heated at 70° C. under a nitrogen atmosphere in 3 ml of dimethyl sulfoxide. After 50 minutes, an aliquot was quenched in methanolic HCl. (By gas chromatography, the reaction is 45% complete.) After 18 hours (overnight), the reaction mixture was cooled to room temperature, diluted with water, and extracted with ether. The organic extracts are shaken with brine, dried (MgSO4) and concentrated to afford methyl 5-(4-trifluoromethylphenoxy)-2-nitrobenzoate in 85% yield. Gas chromatography showed no starting phenol remained. Step B--Methyl 5-(2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoate

Aufarbeitung

  1. customan aliquot was quenched in methanolic HCl
  2. wait) After 18 hours (overnight)
  3. additiondiluted with water
  4. extractionextracted with ether
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dce11846ee5d44c2a50ca89293e122f1
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04395570

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