Diethyl Ether → 5-Bromo-3-pyridinecarboxaldehyde

HRID 910285Notes

Reaction equation

HRID 910285 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[N:17][CH:18]=1.C(OCC)C>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[O:20])[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 27847345-Bromo-3-pyridinecarboxaldehydeYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.5 g (21 mmol) of pyridinium chlorochromate are added at room temperature to a solution of 3 g (16 mmol) of (5-bromopyrid-3-yl)methanol in 70 ml of dichloromethane. After stirring for 1 hour, 70 ml of diethyl ether are added and the reaction medium is again stirred for 1 hour. The precipitate is filtered off through sodium sulfate and the filtrate is evaporated to dryness. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 1 g (35%) of 5-bromopyridine-3-carbaldehyde is obtained.

Workup

  1. stirringthe reaction medium is again stirred for 1 hour
  2. filtrationThe precipitate is filtered off through sodium sulfate
  3. customthe filtrate is evaporated to dryness
  4. customThe residue obtained
  5. customis purified by chromatography on a column of silica
  6. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-e231e33753554b528ab8e552a75f0477
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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