Potassium Cyanide → 2,6-Difluoro-4-iodobenzonitrile

HRID 1034108

반응식

HRID 1034108 반응식
N([O-])=O.[Na+].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[C:9]([F:14])[C:7]=1N.[C-:15]#[N:16].[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>[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[C:9]([F:14])[C:7]=1[C:15]#[N:16]

참가 물질

11

반응물 5

HCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 2789432,6-Difluoro-4-iodoanilineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

생성물 1

HCID 190230682,6-Difluoro-4-iodobenzonitrile

시약·촉매·용매 5

HCID 24463Copper sulfate pentahydrate촉매HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

실험 절차

12 g of sodium nitrite was dissolved in 91 ml of sulfuric acid and cooled to 10° C or less, and then 100 ml of acetic acid was added. At 20 to 25° C, 39 g of the 2,6-difluoro-4-iodoaniline from Step 3 was added to the solution, and then the solution was agitated for one hour. A second solution was made by dissolving 37 g of copper sulfate pentahydrate in 91 ml of water to which was added 62 g of ice, and this solution was added to the first. A third solution containing 39 of potassium cyanide dissolved in 92 ml of water, 221 g of sodium bicarbonate, and 91 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 recrystallized with methanol to obtain 6.7 g of 1,3-difluoro-2-cyano-5-iodobenzene.

후처리

  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. customThis residue was recrystallized with methanol

출처 및 근거

ORD 기록
ord-cd3685bbd7bf4494a31e80b65999d87a
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05314640

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