Hydrochloric Acid → 2-Methyl-4-(trifluoromethyl)benzonitrile

HRID 352451

반응식

HRID 352451 반응식
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1N.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[C-:24]#[N:25].[K+]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CCOCC>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:24]#[N:25]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 137504374-Amino-3-methylbenzotrifluorideHCID 23668193Sodium Nitrite

생성물 1

HCID 222503322-Methyl-4-(trifluoromethyl)benzonitrile수율 88.4%

시약·촉매·용매 3

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매4회HCID 3283Diethyl Ether용매

반응 조건

온도
5 °C

실험 절차

Concentrated hydrochloric acid (16 mL) was added dropwise at a moderate rate to a heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzenamine (14 g, 80 mmol) and 120 mL of water while stirring vigorously. A thick suspension resulted which was stirred for 20 minutes, diluted with 280 mL of water and cooled to 5° C. A solution of sodium nitrite (5.5 g, 80 mmol) and 25 mL of water was added slowly to the reaction suspension. After stirring for 30 minutes at 5° C. a solution resulted which was stirred cold for 30 more minutes and then neutralized with potassium carbonate. This diazonium salt solution was then added portionwise via cannula to a stirred, 95° C. mixture of potassium cyanide (22 g, 0.34 mole), copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water. After the addition the mixture was stirred for 30 minutes at 95° C. and then allowed to cool to room temperature. Ether was added and the heterogeneous mixture was filtered through celite. The solids were washed with ether, and the filtrate was partitioned. The aqueous phase was extracted with ether, and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 13.1 g of the title compound as brown oil.

후처리

  1. customA thick suspension resulted which
  2. stirringwas stirred for 20 minutes
  3. stirringAfter stirring for 30 minutes at 5° C. a solution
  4. customresulted which
  5. stirringwas stirred cold for 30 more minutes
  6. additionAfter the addition the mixture
  7. stirringwas stirred for 30 minutes at 95° C.
  8. temperatureto cool to room temperature
  9. filtrationthe heterogeneous mixture was filtered through celite
  10. washThe solids were washed with ether
  11. customthe filtrate was partitioned
  12. extractionThe aqueous phase was extracted with ether
  13. dry with materialthe combined organic extracts were dried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-80d382ae0ee4470ebd58de5139c9de1c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747047B2

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