Nitrogen → 4-(4-Fluorophenoxy)-1-methyl-2-nitrobenzene

HRID 263436

反応式

HRID 263436 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].N#N>CCOCC.N1C=CC=CC=1>[N+:9]([C:4]1[CH:3]=[C:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[CH3:8])([O-:11])=[O:10]

参加物

7

反応物 4

HCID 947NitrogenHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 1235464-Bromo-2-nitrotoluene

生成物 1

HCID 35376734-(4-Fluorophenoxy)-1-methyl-2-nitrobenzene収率 63.1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
90 °C

実験手順

4-Bromo-2-nitrotoluene (25.0g, 116 mmol), 4-fluorophenol (8.70g, 77.6 mmol), potassium carbonate (21.5g, 156 mmol) and pyridine (75 mL), were combined under N2 atmosphere and heated at 90° C. for 30 min. The reaction mixture was cooled to ambient temperature, CuO (15.4g, 194 mmol) was added under a stream of N2, and the resulting dark-brown suspension was heated at reflux for 17 hours. The reaction mixture was cooled to ambient temperature and diluted with ether. The solids were removed by filtration through celite. The ethereal solution was washed with 1.0M aqueous NaOH, 1.0M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a dark-brown oil. The crude product was purified by chromatography on silica gel to give 2-nitro-4-(4-fluorophenoxy)-toluene (12.1 g, 63%).

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. temperaturethe resulting dark-brown suspension was heated
  3. temperatureat reflux for 17 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. customThe solids were removed by filtration through celite
  6. washThe ethereal solution was washed with 1.0M aqueous NaOH, 1.0M aqueous HCl and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a dark-brown oil
  11. customThe crude product was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-2111e3ecfd044200b27d59782b961da2
出典データセット
uspto-grants-1997_07
特許番号
US05643922

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