Potassium Cyanide → 2-Fluoro-4-iodobenzonitrile

HRID 1034111Notes

Reaction equation

HRID 1034111 reaction equation
N([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1N.[C-:14]#[N:15].[K+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].C1C=CC=CC=1.C(O)(=O)C>[C:14]([C:7]1[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:6]=1[F:5])#[N:15]

Participants

11

Reactant 5

HCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 1856942-Fluoro-4-iodoanilineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 27745182-Fluoro-4-iodobenzonitrileYield 29.5%

Reagents, catalysts & solvents 5

HCID 24463Copper sulfate pentahydrateCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

27 g of sodium nitrite was dissolved in 205 ml of sulfuric acid and cooled to 10° C. or less, and then 238 ml of acetic acid was added. At 20° to 25° C., 65 g of 2-fluoro-4-iodoaniline was added to the solution, and then the solution was agitated for one hour. A second solution was made by dissolving 82.5 g of copper sulfate pentahydrate in 20.5 ml of water, to which was added 140 g of ice, and this solution was added to the first. A third solution containing 88 g of potassium cyanide dissolved in 207 ml of water, 500 g of sodium bicarbonate, and 206 ml of benzene was added to the first solution, and a diazonium salt sulfuric acid solution was added therein. After agitation at room temperature for 3 hours, a sodium hydroxide aqueous solution was added to dissolve the crystals. After being extracted with chloroform, the crystals were washed three times alternating with a 10% sodium hydroxide solution and water. After distillation of the chloroform, the residue was extracted with hexane, and the hexane was distilled off. This residue was subjected to vacuum distillation (95° to 110° C./15 mmHg), and further recrystallized to obtain 20 g of 1-cyano-2-fluoro-4-iodobenzene.

Workup

  1. temperaturecooled to 10° C. or less
  2. additionthis solution was added to the first
  3. waitAfter agitation at room temperature for 3 hours
  4. dissolutionto dissolve the crystals
  5. extractionAfter being extracted with chloroform
  6. washthe crystals were washed three times
  7. distillationAfter distillation of the chloroform
  8. extractionthe residue was extracted with hexane
  9. distillationthe hexane was distilled off
  10. distillationThis residue was subjected to vacuum distillation (95° to 110° C./15 mmHg)
  11. customfurther recrystallized

Sources & evidence

ORD record
ord-6c4afcb0019747d1ab02f0eeafc1bcd1
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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