Dimethylformamide → 1-Nitro-2-(2,2,2-trifluoroethoxy)benzene

HRID 342542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342542
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C1(C)C=CC(S(O[CH2:21][C:22]([F:25])([F:24])[F:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:23][C:22]([F:25])([F:24])[CH2:21][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Produkt 1

HCID 27757681-Nitro-2-(2,2,2-trifluoroethoxy)benzeneAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2-nitrophenol (18.8 g, 135 mmol), 2,2,2-trifluoroethyl para-toluenesulfonate (34.36 g, 135 mmol), potassium carbonate (18.7 g, 135 mmol) and DMF (200 mL) was heated 16 hours at 140° C. The reaction mixture then was cooled, diluted with water (600 mL) and extracted with ether/hexanes (1:1; 3×400 mL). The combined extracts were washed with saturated sodium bicarbonate (3×100 mL) and brine, dried (Na2SO4), filtered and concentrated to give 1-(2,2,2-trifluoroethoxy)-2-nitrobenzene (27 g, 117 mmol) as an oil.

Aufarbeitung

  1. temperatureThe reaction mixture then was cooled
  2. extractionextracted with ether/hexanes (1:1; 3×400 mL)
  3. washThe combined extracts were washed with saturated sodium bicarbonate (3×100 mL) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05fa67918df447f983d422c8f6180996
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859014

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