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

HRID 1294058ノート

反応式

HRID 1294058 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c2cbc1d491f14c8788e58d6cdfabb9d5
出典データセット
uspto-grants-2007_07
特許番号
US07238813B2

反応ノート

読み込み中…