Cornforth reagent → 6-Bromo-4-iodonicotinaldehyde

HRID 468885Notes

Reaction equation

HRID 468885 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([I:10])[CH:3]=1.[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]=[C:4]([I:10])[C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86674964(6-Bromo-4-iodopyridin-3-yl)methanol

Product 1

HCID 574695636-Bromo-4-iodonicotinaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (6-bromo-4-iodopyridin-3-yl)methanol (300 mg, 1.0 mmol) and pyridinium dichromate (720 mg, 1.9 mmol) in methylene chloride (4 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with methylene chloride (20 mL), filtered over Celite, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-40% ethyl acetate in heptane) to afford the title compound as a white solid (180 mg, 60%), which was used in the next step without further purification.

Workup

  1. filtrationfiltered over Celite
  2. customevaporated in vacuo
  3. customto afford a residue that
  4. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-26878bd822014156b2d964c9df6841d5
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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