Sodium Iodide → 1-Bromo-4-(1-methyl-hexyloxy)-benzene

HRID 2099035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099035
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[CH3:9][CH:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC.O>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:10]([CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:1][CH:2]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 160902-Bromoheptane

Produkt 1

HCID 200967851-Bromo-4-(1-methyl-hexyloxy)-benzeneAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

p-Bromophenol (295.52 grams (“g”), 1500.00 millimole) is dissolved in anhydrous dimethyl formamide (“DMF”) (500 milliliters) in a 2000 milliliter (“mL”) 3-necked flask equipped with mechanical stirrer and condenser, under an argon atmosphere. To this solution, (1-methyl)hexylbromide (322.38 grams, 1800.00 millimoles), sodium iodide (33.57 g, 225.00 mmol) and anhydrous potassium carbonate (621.95 g, 4500.00 mmol) are added. The resulting suspension is heated to 100° C. and stirred at that temperature for 72 hours. After cooling to room temperature, water (1000 mL) and n-hexane (300 mL) are added. The aqueous layer is separated and extracted with n-hexane (3×100 mL). The combined organic layers are washed with diluted sodium chloride solution (2×100 mL) and dried (MgSO4). The solvent is removed by rotary evaporation under reduced pressure and the residue is filtered using a SiO2 layer (10×10 cm) and n-hexane as eluent. After removal of solvent by rotary evaporation and in vacuo a colorless liquid (245.54 g, 60%) is obtained.

Aufarbeitung

  1. customequipped with mechanical stirrer and condenser, under an argon atmosphere
  2. temperatureAfter cooling to room temperature
  3. customThe aqueous layer is separated
  4. extractionextracted with n-hexane (3×100 mL)
  5. washThe combined organic layers are washed with diluted sodium chloride solution (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed by rotary evaporation under reduced pressure
  8. filtrationthe residue is filtered
  9. customAfter removal of solvent
  10. customby rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-d5c2aaa7d3d64341b08fcb6fcbab8a7f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569415B2

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