Sodium Iodide → 4-Bromo-2-methyl-1-(2-propoxyethoxy)benzene

HRID 1978633

Reaktionsgleichung

Reaktionsgleichung von HRID 1978633
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24])=[C:4]([CH3:9])[CH:3]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenolHCID 1235061-(2-Chloroethoxy)propane

Produkt 1

HCID 219957224-Bromo-2-methyl-1-(2-propoxyethoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-bromo-2-methylphenol (10.46 g) in DMF (10 ml) were added at room temperature potassium carbonate (11.5 g), sodium iodide (9.97 g) and 2-chloroethylpropylether (5.6 ml), and the mixture was stirred at 90° C. for 7 days. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N sodium hydroxide solution and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:9) to give pale yellow oil of 4-bromo-2-methyl-1-(2-propoxyethoxy)benzene (11.7 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, 1N sodium hydroxide solution and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-83f2cc12a1c74876b2daf50e74f3f241
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235771B1

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