HCID 18786121, compound → HCID 18786118, compound

HRID 1107877Notes

Reaction equation

HRID 1107877 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]2[C:12]([Br:13])=[CH:11][CH:10]=[CH:9][C:6]=2[C:7]=1[CH3:8]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:4][C:5]2[C:12]([Br:13])=[CH:11][CH:10]=[CH:9][C:6]=2[C:7]=1[CH3:8])=[O:1]

Participants

4

Reactant 1

HCID 18786121HCID 18786121, compound

Product 1

HCID 18786118HCID 18786118, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

0.7 g (7.92 mmol) of manganese dioxide is added to a solution of 0.38 g (1.58 mmol) of 2-hydroxymethyl-3-methyl-7-bromobenzofuran in 10 ml of dichloromethane. The solution is stirred at room temperature for 16 h and 0.7 g (7.92 mmol) of manganese dioxide is again added. After stirring for 24 h at room temperature, the manganous precipitate is filtered off and the filtrate is concentrated under vacuum. The residue is purified by silica column chromatography (elution solvent: 10% ethyl acetate in cyclohexane). 0.25 g (Yield: 66%) of 2-formyl-3-methyl-7-bromobenzofuran is obtained in the form of a yellow wax.

Workup

  1. stirringAfter stirring for 24 h at room temperature
  2. filtrationthe manganous precipitate is filtered off
  3. concentrationthe filtrate is concentrated under vacuum
  4. customThe residue is purified by silica column chromatography (elution solvent: 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-6d4b1b2bde054806901c69016ea7b9d2
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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