Potassium Cyanide → 2-Fluoro-4-methylbenzonitrile

HRID 1371040Notes

Reaction equation

HRID 1371040 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].C([O-])(O)=O.[Na+].[C-]#N.[K+].[C:22]([Cu])#[N:23]>Cl>[F:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[C:22]#[N:23]

Participants

7

Reactant 5

HCID 9032Potassium CyanideHCID 679842-Fluoro-4-methylanilineHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 27784432-Fluoro-4-methylbenzonitrileYield 98.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

2-Fluoro-4-methylaniline (15 g, 120 mmol, 1 eq) was dissolved in 600 ml 1M HCl at 0° C. and a 120 ml aqueous solution of sodium nitrite (12.4 g, 180 mmol, 1.5 eq) was added dropwise, maintaining the temperature under 5° C. The solution was neutralized with solid NaHCO3 and poured into a 600 ml aqueous solution of 36 g KCN and 23.8 g CuCN at 60° C. The solution was stirred for 30 min and cooled to RT. The product was extracted 3 times with EtOAc and the combined organic layers were washed with brine and dried with sodium sulfate. The solvent was removed and 16 g (98%) of product was obtained.

Workup

  1. temperaturecooled to RT
  2. extractionThe product was extracted 3 times with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-241692956f784be7ab1d52a08d685245
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

Loading…