Acetyl chloride → Phenol, 4-bromo-, 1-acetate

HRID 1408634

Reaktionsgleichung

Reaktionsgleichung von HRID 1408634
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>C(Cl)Cl>[C:5]([O:16][C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 78084-BromophenolHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 74726Phenol, 4-bromo-, 1-acetateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Anhydrous aluminum chloride (84 g, 0.486 mol) was suspended in methylene chloride (1200 mL), and then acetyl chloride (49.2 g, 0.629 mol) was added while stirring and cooling on ice. The mixture was stirred for 20 minutes while cooling on ice and 4-bromophenol (98 g, 0.57 mol) was added. The reaction mixture was stirred at room temperature for 1 h, and then ice water was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography to yield 4-bromophenyl acetate (104 g, 85%). 1H-NMR (CDCl3): 2.28 (s, 3H), 6.98 (d, 2H), 7.48 (d, 2H).

Aufarbeitung

  1. temperaturecooling on ice
  2. stirringThe mixture was stirred for 20 minutes
  3. additionwas added
  4. stirringThe reaction mixture was stirred at room temperature for 1 h
  5. extractionextraction
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a4a4a5f9eccb455a8ee7ff5558c42152
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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