HCID 12792392, compound → 1-(4-Bromo-2-thienyl)ethan-1-one

HRID 1386493Notes

Reaction equation

HRID 1386493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([OH:9])[CH3:8])[S:5][CH:6]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:7](=[O:9])[CH3:8])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 12792392HCID 12792392, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 27352371-(4-Bromo-2-thienyl)ethan-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of raw 4-bromo-2-(1′-hydroxyethyl)thiophene (1.28 g, 6.18 mmol) and PCC (2.6 g, 13.26 mmol) in 20 ml of dichloromethane is put into a flask fitted with magnetic stirring and under an atmosphere of argon. It is agitated vigorously for 2 hours at ambient temperature, the reaction medium becoming progressively black. It is then filtered on a column of florisil (eluent ether), the solvent evaporated and the raw product produced is purified by flash chromatography on silica (eluent pure petroleum ether). 1.10 g of a white solid is obtained 4-bromo-2-acetyl-thiophene (yield=87%).

Workup

  1. customfitted
  2. stirringIt is agitated vigorously for 2 hours at ambient temperature
  3. customthe reaction
  4. filtrationIt is then filtered on a column of florisil (eluent ether)
  5. customthe solvent evaporated
  6. customthe raw product produced
  7. customis purified by flash chromatography on silica (eluent pure petroleum ether)

Sources & evidence

ORD record
ord-8ba924b0752b498aa2d38f1d856e3b70
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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