p-Fluoronitrobenzene → Benzenamine, 2-nitro-4-(4-nitrophenoxy)-

HRID 1294058노트

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HRID 1294058 반응식
[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:1][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 37588824-Amino-3-Nitrophenol

생성물 1

HCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of 4-hydroxy-2-nitroaniline (3.08 g, 20.0 mmol) in DMF (30 mL) was added NaH (60% oily, 880 mg, 22.0 mmol) followed by 1-fluoro-4-nitrobenzene (2.33 mL, 22.0 mmol). The mixture was stirred at 90° C. overnight. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (4.56 g, 83%): MS m/e 274 (M−1).

후처리

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthen evaporated
  6. customSequence purification on SiO2 column chromatography

출처 및 근거

ORD 기록
ord-c2cbc1d491f14c8788e58d6cdfabb9d5
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238813B2

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