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

HRID 2266169Notes

Reaction equation

HRID 2266169 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-3cdfceddb2b9437e99ec3c6f1865611b
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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