Water → 2-Nitro-5-(4-chlorophenoxy)benzonitrile

HRID 1734621노트

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HRID 1734621 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([CH:17]=1)[C:15]#[N:16].O.[OH-].[Na+]>CN(C)C=O>[N+:18]([C:13]1[CH:12]=[CH:11][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][C:14]=1[C:15]#[N:16])([O-:20])=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 1005065-Chloro-2-nitrobenzonitrile

생성물 1

HCID 218248742-Nitro-5-(4-chlorophenoxy)benzonitrile수율 52.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether. The petroleum ether was decanted, and the sodium hydride was suspended in about 20 mL of N,N-dimethylformamide. The suspension was stirred, and solutions of 4.5 grams (0.035 mole) of 4-chlorophenol in 20 mL of N,N-dimethylformamide and 5.0 grams (0.027 mole) of 5-chloro-2-nitrobenzonitrile in 20 mL of N,N-dimethylformamide were added, respectively. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred for about 18 hours. The reaction mixture was then cooled and poured into a mixture of 500 mL of water and 50 mL of aqueous 2N sodium hydroxide. The mixture was stirred for about 15 minutes, then it was allowed to stand for about 18 hours. The resultant solid was collected by filtration and recrystallized from ethanol, yielding 3.9 grams of 2-nitro-5-(4-chlorophenoxy)benzonitrile, mp 120°-122° C. The NMR spectrum was consistent with the proposed structure.

후처리

  1. washSodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether
  2. customThe petroleum ether was decanted
  3. additionUpon completion of addition
  4. temperaturethe reaction mixture was warmed
  5. temperatureto reflux where it
  6. stirringstirred for about 18 hours
  7. temperatureThe reaction mixture was then cooled
  8. stirringThe mixture was stirred for about 15 minutes
  9. filtrationThe resultant solid was collected by filtration
  10. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-bf5fb274188a445ba43d2a3cdbf96a9a
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534518

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