Acetyl chloride → Phenol, 3-bromo-, 1-acetate

HRID 82747

Reaktionsgleichung

Reaktionsgleichung von HRID 82747
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:11])[CH3:10]>N1C=CC=CC=1.ClCCl>[C:9]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:11])[CH3:10]

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 115633-Bromophenol

Produkt 1

HCID 141946Phenol, 3-bromo-, 1-acetateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-bromophenol (50 g, 0.29 mol) in pyridine (200 mL) and dichloromethane (100 mL) was added dropwise acetyl chloride (25 mL, 0.35 mol) at 0° C. and the mixture was stirred 18 h at room temperature. LC-MS showed that the reaction was complete. Pyridine and dichloromethane was evaporated in vacuo. Water (600 mL) was added and acidified with hydrochloric acid at pH 2. The reaction mixture was extracted with ethyl acetate (500 mL×3) and the organic phase was dried over anhydrous sodium sulfate, filtrated, concentrated and purified by column chromatography (PE:EA=60:1) to afford compound E-1 as a colorless liquid (46 g, 74%).

Aufarbeitung

  1. customPyridine and dichloromethane was evaporated in vacuo
  2. additionWater (600 mL) was added
  3. extractionThe reaction mixture was extracted with ethyl acetate (500 mL×3)
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. custompurified by column chromatography (PE:EA=60:1)

Quellen und Nachweise

ORD-Eintrag
ord-e967a84eaca949648371400592c1fba9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846736B2

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