(4-Bromo-1-benzofuran-2-yl)methanol → 4-Bromo-1-benzofuran-2-carbaldehyde

HRID 1740300Notes

Reaction equation

HRID 1740300 reaction equation
[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][OH:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21838195(4-Bromo-1-benzofuran-2-yl)methanol

Product 1

HCID 218380444-Bromo-1-benzofuran-2-carbaldehydeYield 80.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-2-hydroxymethylbenzofuran (0.3 g) and manganese dioxide (0.75 g) in ethyl acetate (3 ml) was heated to reflux for 4 hours. Manganese dioxide was removed by filtration and washed with ethyl acetate. Ethyl acetate was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1) to give 4-bromo-2-formylbenzofuran (0.24 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customManganese dioxide was removed by filtration
  4. washwashed with ethyl acetate
  5. customEthyl acetate was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-1e7937f2439c4a0b97d11ab3bfc298ef
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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