Cornforth reagent → 5-Bromo-2-ethoxybenzaldehyde

HRID 2257806Notes

Reaction equation

HRID 2257806 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([CH:9]=1)[CH2:7][OH:8].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 247216395-Bromo-2-ethoxybenzyl alcohol

Product 1

HCID 1449015-Bromo-2-ethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-2-ethoxybenzyl alcohol (2.78 g, 12.0 mmol) and pyridinium dichromate (4.51 g, 12.0 mmol) in 120 ml of CH2Cl2 was stirred at RT for 6 h. The mixture was filtered, washed with H2O, 0.5N HCl and brine and dried over Na2SO4. The product was purified by silica gel column chromatography (EtOAc/petroleum ether 10:100) to give 5-bromo-2-ethoxybenzaldehyde.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with H2O, 0.5N HCl and brine
  3. dry with materialdried over Na2SO4
  4. customThe product was purified by silica gel column chromatography (EtOAc/petroleum ether 10:100)

Sources & evidence

ORD record
ord-3747722cd3434d0781851750915a78c8
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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