Hydrogen Peroxide → 5-Cyano-2-fluorobenzoic acid

HRID 1934698Notes

Reaction equation

HRID 1934698 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])#[N:2].P([O-])(O)(O)=[O:13].[Na+].OO.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[C:8]([OH:13])=[O:9])#[N:2]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 109097255-Cyano-2-fluorobenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 27784625-Cyano-2-fluorobenzoic acidYield 432.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-cyano-2-fluorobenzaldehyde (145 mg) in acetonitrile (2 mL) were added a sodium dihydrogenphosphate aqueous solution (23 mg in 1 mL water) and 30% hydrogen peroxide (0.09 mL). To the resulting mixture was added dropwise a sodium chlorite aqueous solution (126mg in 1 mL water) for an hour at 0° C. The mixture was stirred for an hour at ambient temperature, then a small amount of sodium sulfite was added. The mixture was diluted with ethyl acetate and washed successively with 1N-hydrochloric acid and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 5-cyano-2-fluorobenzoic acid (137 mg) as a solid substance.

Workup

  1. washwashed successively with 1N-hydrochloric acid and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-2d6331484ba2479cb352d3664d6b793a
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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