Water → 4-Fluorobenzonitrile

HRID 1161717Notes

Reaction equation

HRID 1161717 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10]O.Cl.[Na+].[I-].O>C(#N)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 680234-FluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 145174-FluorobenzonitrileYield 77.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 4-fluoro benzaldehyde (8 g, 64 mmol) in acetonitrile (100 mL) was added NH2OH.HCl (5.78 g, 83 mmol) and NaI (4.8 g, 32 mmol) with stirring. The mixture was then stirred for 7 hours at refluxing temperature, cooled at the temperature in the range of 20-40° C., poured into water (200 mL) and extracted with EtOAc (2×250 mL). The organic layers were collected, combined, washed with brine solution, dried over anhydrous Na2SO4 and concentrated under vacuum to give the 4-fluoro-benzonitrile (6.0 g, 76% yield).

Workup

  1. stirringThe mixture was then stirred for 7 hours
  2. temperatureat refluxing temperature
  3. extractionextracted with EtOAc (2×250 mL)
  4. customThe organic layers were collected
  5. washwashed with brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-44807a809d9c46ffa89811d308fd54f5
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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