4-Nitrophenol → 1-(2-Bromoethoxy)-4-nitrobenzene

HRID 37841ノート

反応式

HRID 37841 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19]Br>CC(=O)CC>[Br:17][CH2:18][CH2:19][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 9804-NitrophenolHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

生成物 1

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzene収率 70.7%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of p-nitro-phenol (6.0 g, 43.1 mmol), potassium carbonate (14.9 g, 108 mmol) and 1,2-dibromoethane (24.3 g, 129 mmol) in butanone (80 mL) was heated at reflux for 18 h. The mixture was cooled, the inorganic salts filtered and the filtrate concentrated under vacuum to give a brown viscous liquid, which was partitioned between dichloromethane and water. The organic phase was separated and concentrated in vacuo to obtain a residue which was purified by column chromatography using 4% ethyl acetate in petroleum ether as eluent to afford 1-(2-bromo-ethoxy)-4-nitro-benzene (7.5 g, 70%) as a light yellow solid.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureThe mixture was cooled
  4. filtrationthe inorganic salts filtered
  5. concentrationthe filtrate concentrated under vacuum
  6. customto give a brown viscous liquid, which
  7. customwas partitioned between dichloromethane and water
  8. customThe organic phase was separated
  9. concentrationconcentrated in vacuo
  10. customto obtain a residue which
  11. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-d92c74dec56243feb3f871ceca7d81c6
出典データセット
uspto-grants-2013_09
特許番号
US08524705B2

反応ノート

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