Acetyl chloride → Acetic acid 4-bromo-2-ethyl-phenyl ester

HRID 858569

Reaktionsgleichung

Reaktionsgleichung von HRID 858569
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][CH3:21])[CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:1](=[O:3])[CH3:2])=[C:15]([CH2:20][CH3:21])[CH:14]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 878774-Bromo-2-ethylphenol

Produkt 1

HCID 12920976Acetic acid 4-bromo-2-ethyl-phenyl esterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetyl chloride (1.06 mL, 14.9 mmol) followed by triethylamine (2.08 mL, 14.9 mmol) were added to a cooled 0° C. solution of 4-Bromo-2-ethyl-phenol (2.5 g, 12.4 mmol, from Step 1) dissolved in CH2Cl2. The reaction was stirred for 2 hrs and then partitioned between 1 N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to a brown oil. The oil was purified by silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a clear oil (2.44 g, 81%).

Aufarbeitung

  1. custompartitioned between 1 N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil
  5. customThe oil was purified by silica gel chromatography (0% to 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c5e4098ac1994fd5aa5366136ac946ab
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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