Ethyl Acetate → 2,4-Dimethoxy-5-fluoronitrobenzene

HRID 649854

Reaktionsgleichung

Reaktionsgleichung von HRID 649854
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[O-]S(C(F)(F)[F:19])(=O)=O.ClC1C=[N+](F)C=C(Cl)C=1.C(OCC)(=O)C>ClCC(Cl)(Cl)Cl>[F:19][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 786332,4-Dimethoxy-1-nitrobenzeneHCID 27245783,5-Dichloro-1-fluoropyridinium triflate2×

Produkt 1

HCID 27584142,4-Dimethoxy-5-fluoronitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 124181,1,1,2-TetrachloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2,4-dimethoxy-nitrobenzene (1.0 g) in tetrachloroethane (10 mL) is added 3,5-dichloro-1-fluoro-pyridinium triflate (85%, 5.07 g) and the mixture is heated to 120° C. for 5 hours. Additional 3,5-dichloro-1-fluoro-pyridinium triflate (85%, 0.25 g) is added and heating is continued for 1 hour. The solution is then cooled to room temperature and passed over a column of silica gel (hexanes followed by 30% ethyl acetate in hexanes is used as the eluant). Product containing fractions are combined, evaporated under reduced pressure, and the residue is crystallized from hexanes to provide the desired product as a tan solid.

Aufarbeitung

  1. temperatureheating
  2. temperatureThe solution is then cooled to room temperature
  3. additionProduct containing fractions
  4. customevaporated under reduced pressure
  5. customthe residue is crystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-beefefe3761740c4b3b00c80aa88b061
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271236B1

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