Methyl iodide → 2-Methoxy-1-nitro-3-(trifluoromethyl)benzene

HRID 501548

Reaktionsgleichung

Reaktionsgleichung von HRID 501548
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[OH:14])([O-:3])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:5]=1[O:14][CH3:15])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9018342-Nitro-6-(trifluoromethyl)phenol

Produkt 1

HCID 219358692-Methoxy-1-nitro-3-(trifluoromethyl)benzeneAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a suspension of compound 17A (1.4 g, 6.76 mmol) and K2CO3 (1.4 g, 10 mmol) in DMF (60 mL) was added iodomethane (0.46 mL, 7.44 mmol). After the addition, the mixture was stirred at 40° C. overnight, then cooled to rt, partitioned between ether and water. The separated ether layer was washed with water and brine, then dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 10% EtOAc/hexane to yield the title compound (1.38 g, 92% yield).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturecooled to rt
  3. custompartitioned between ether and water
  4. washThe separated ether layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-de7f567ea8e64129af6501cea2e3c36b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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