Water → 1-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

HRID 419414

Reaktionsgleichung

Reaktionsgleichung von HRID 419414
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:13][O:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 225037424-Chloro-5-fluoro-2-nitrophenol

Produkt 1

HCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chloro-5-fluoro-2-nitrophenol (2.29 g, 12.0 mmol) was dissolved in DMF (25 mL). K2CO3 (2.5 g, 18 mmol) and iodomethane (0.893 mL, 14.3 mmol) were added and the mixture was stirred at rt overnight. The mixture was then poured into H2O and extracted with EtOAc (2×) and then the combined organics were extracted with H2O (5×). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to give the title compound of step B without further purification (2.19 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (dd, J=7.8, 1.0 Hz, 1H), 7.54 (d, J=11.4 Hz, 1H), 3.90 (d, J=1.1 Hz, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. extractionthe combined organics were extracted with H2O (5×)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-53e6aceaee554e018d6d67e9b12ffe56
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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