Methyl iodide → 1,2,4-Trimethoxy-5-nitrobenzene

HRID 1179220

Reaktionsgleichung

Reaktionsgleichung von HRID 1179220
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([OH:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[C:6]([O:11][CH3:15])=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2971214,5-Dimethoxy-2-nitrophenol

Produkt 1

HCID 8224151,2,4-Trimethoxy-5-nitrobenzeneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

A mixture of 4,5-dimethoxy-2-nitro-phenol (2.00 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol) and iodomethane (0.75 mL, 12 mmol) in DMF was placed in a sealed tube and heated at 75-80° C. for 20 h. The reaction was cooled and was filtered through Celite, washing with ethyl acetate. The filtrate was washed with water (the first wash was back-extracted with ethyl acetate), sodium bicarbonate and brine, was dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 1:1 ethyl acetate:hexanes provided 1,2,4-trimethoxy-5-nitro-benzene (1.20 g, 57% yield) as a yellow solid. 1H-NMR (CDCl3, 500 MHz) 7.53 (s, 1H), 6.50 (s, 1H), 3.92 (s, 3H), 3.91 (s, 3H), 3.84 (s, 3H) ppm; MS (FIA) 214.1 (M+H); HPLC (Method A) 3.253 min.

Aufarbeitung

  1. customwas placed in a sealed tube
  2. temperatureThe reaction was cooled
  3. filtrationwas filtered through Celite
  4. washwashing with ethyl acetate
  5. washThe filtrate was washed with water (the
  6. washfirst wash
  7. extractionwas back-extracted with ethyl acetate), sodium bicarbonate and brine
  8. dry with materialwas dried (sodium sulfate)
  9. customwas evaporated
  10. customPurification by flash chromatography (SiO2)
  11. washeluted with 1:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-48df0215a847437ebf83cec48b249f75
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279469B2

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