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

HRID 81840

Reaction equation

HRID 81840 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneYield 60.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-76f42d179a9649d9adac111f50b164eb
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Linked notes

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