1-Bromo-2-methylpropane → 1-Bromo-4-(2-methylpropoxy)benzene

HRID 1515443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515443
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH:16]([CH3:18])[CH3:17]>CC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 78084-BromophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 153241111-Bromo-4-(2-methylpropoxy)benzeneAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Bromo-phenol (2 g, 11.6 mmol) is dissolved in acetone (40 mL). Potassium carbonate (8 g, 38.4 mmol) is then added followed by isobutyl bromide (4 g, 29.2 mmol). The reaction is heated to reflux for four days, refilling solvent as necessary. The reaction mixture is diluted with water and extracted with ether, the organic layer is separated and concentrated in vacuo. The residue is dissolved in hexane dried with magnesium sulfate, and filtered through a plug of silica gel. The solvent is removed in vacuo to afford 1.6 g (60% yield) of the title compound as a colorless non-viscous oil. 1H NMR (CDCl3) δ 1.01 (d, 6H, J=6.56 Hz), 2.05-2.08 (m, 1H), 3.67 (d, 2H, J=6.57 Hz), 6.77 (d, 2H, J=9.09 Hz), 7.36 (d, 2H, J=9.09 Hz).

Aufarbeitung

  1. temperatureThe reaction is heated
  2. temperatureto reflux for four days
  3. extractionextracted with ether
  4. customthe organic layer is separated
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in hexane
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered through a plug of silica gel
  9. customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11553213c5de40959df2fedb8bbf83ae
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222424B2

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