Sulfuric Acid → 2-Methyl-3,4,6-trifluorobenzonitrile

HRID 864328

반응식

HRID 864328 반응식
[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[C-:21]#[N:22].[K+].[OH-].[NH4+]>S([O-])([O-])(=O)=O.[Cu+2].O>[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1[C:21]#[N:22]

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 226251783,4,6-Trifluoro-2-methylanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 226251752-Methyl-3,4,6-trifluorobenzonitrile수율 38.2%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 962Water용매2회

실험 절차

To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), potassium cyanide (43 g), ammonium hydroxide (60 ml) and water (260 ml) at 10°-30° C. The mixture is extracted with dichloromethane and the extract is dried over sodium sulfate, concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane: n-hexane=1:4) to give 2-methyl-3,4,6-trifluorobenzonitrile (4.3 g).

후처리

  1. temperaturethe mixture is cooled
  2. extractionThe mixture is extracted with dichloromethane
  3. dry with materialthe extract is dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified with column chromatography (silica-gel, dichloromethane: n-hexane=1:4)

출처 및 근거

ORD 기록
ord-ba3974c965aa4638a48c1a9eb50065a3
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563138

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