1-(4-Bromo-2-thienyl)-1-propanol → 4-Bromo-2-propionylthiophene

HRID 49341

Reaction equation

HRID 49341 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([OH:10])[CH2:8][CH3:9])[S:5][CH:6]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([C:7](=[O:10])[CH2:8][CH3:9])[S:5][CH:6]=1

Participants

4

Reactant 1

HCID 226069011-(4-Bromo-2-thienyl)-1-propanol

Product 1

HCID 8189324-Bromo-2-propionylthiophene

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

33.5 g (151 mmol) of 1-(4-bromo-2-thienyl)-1-propanol are dissolved in 400 mL of dichloromethane. 130 g (1.5 mol) of manganese dioxide are then added portionwise and the medium is stirred at room temperature for 24 hours. After filtration through Celite and then concentration and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate), the desired product is obtained in the form of white crystals (m=26.6 g; Y=80%).

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationconcentration and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate)

Sources & evidence

ORD record
ord-5d27fd9b2e004ef1b5d56e425461e493
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Linked notes

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