Benzyl Chloride → 4-(Benzyloxy)-1-bromo-2-chlorobenzene

HRID 269887

Reaktionsgleichung

Reaktionsgleichung von HRID 269887
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([Cl:9])[CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 70181824-Bromo-3-chlorophenol

Produkt 1

HCID 223195014-(Benzyloxy)-1-bromo-2-chlorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-bromo-3-chlorophenol (2.5 g), potassium carbonate (2.165 g) and N,N-dimethylformamide (26 mL), benzyl chloride (1.8 mL) was added under cooling with ice. Raising the temperature to the ambient level, the system was stirred for 23 hours. The reaction mixture was poured in saturated saline solution and the product was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, and dried over anhydrous magnesium sulfate. Distilling the solvent off, the remaining crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=10:1) to provide 4-benzyloxy-1-bromo-2-chlorobenzene (3.029 g).

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. temperatureRaising the temperature to the ambient level
  4. additionThe reaction mixture was poured in saturated saline solution
  5. extractionthe product was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationDistilling the solvent off, the remaining crude product
  9. customwas purified on silica gel column chromatography (eluent, hexane: ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-bbc75ee7135a4452a2b7035e0af7741b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449466B2

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