Cornforth reagent → 5-Fluoro-2-nitrobenzaldehyde

HRID 910105Notes

Reaction equation

HRID 910105 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 12016493(5-Fluoro-2-nitrophenyl)methanol

Product 1

HCID 5870905-Fluoro-2-nitrobenzaldehydeYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Dissolve (5-fluoro-2-nitrophenyl)methanol (13.92 g, 81.08 mmol) in dichloromethane (284 mL). Add 4 Å molecular sieves (73 g) and pyridinium dichromate (36.58 g, 97.3 mmol). Stir the mixture at 20° C. for 6 hours. Filter the crude reaction mixture through a short silica gel column. Remove the solvent under reduced pressure and purify the residue by flash chromatography (silica gel, 10-20% ethyl acetate/hexane) to obtain 9.43 g (69%) of title compound as colorless oil.

Workup

  1. filtrationFilter the crude
  2. customreaction mixture through a short silica gel column
  3. customRemove the solvent under reduced pressure
  4. custompurify the residue by flash chromatography (silica gel, 10-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a0c3efa4ca3b4a5792336ff0dfb9f37e
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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