Cornforth reagent → 5-Bromo-2-ethoxybenzaldehyde

HRID 861622

Reaction equation

HRID 861622 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 24721639(5-Bromo-2-ethoxyphenyl)methanol

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-14ed117b41fe4638a869c64991c7f68e
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Linked notes

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