Acetic Acid → 2-Bromo-1-thiophen-3-yl-butan-1-one

HRID 1677341

Reaktionsgleichung

Reaktionsgleichung von HRID 1677341
[S:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:10])[CH2:7][CH2:8][CH3:9])=[CH:2]1.C(O)(=O)C.[Br:15]Br>C(OCC)C>[Br:15][CH:7]([CH2:8][CH3:9])[C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24408BromineHCID 201580431-(Thiophen-3-yl)butan-1-one

Produkt 1

HCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-Thiophen-3-yl-butan-1-one (6.7 g. 43 mmol) in 210 mL diethyl ether was cooled to zero degrees C., and 0.6 ml glacial acetic acid was added dropwise, followed by bromine (2.26 ml, 46 mmol) dropwise. The reaction mixture was allowed to warm to room temperature over hours. The reaction mixture was washed the with water, 1 N sodium thiosulfate, brine, and then dried over magnesium sulfate. Solvent was removed under reduced pressure to give an oil which was chromatographed (5% EtOAc/Hexanes) to give 6.1 g 2-Bromo-1-thiophen-3-yl-butan-1-one, 79%, as an oil.

Aufarbeitung

  1. washThe reaction mixture was washed the with water, 1 N sodium thiosulfate, brine
  2. dry with materialdried over magnesium sulfate
  3. customSolvent was removed under reduced pressure
  4. customto give an oil which
  5. customwas chromatographed (5% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e823679ea8b443148ec162a13818710a
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008313B2

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