Isopropyl iodide → 2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene

HRID 1420825ノート

反応式

HRID 1420825 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

生成物 1

HCID 187825712-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene収率 94%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 2-bromo-4-nitrophenol (Description 40, 2.5 g), 2-iodopropane (2.2 g) and potassium carbonate (5 g) in acetone (30 ml) was heated under reflux for 18 h. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (90:10) to give the title compound (2.8 g, 94%). 1H NMR (250 MHz, CDCl3) δ8.46 (1H, s), 8.20 (1H, m), 6.93 (1H, m), 4.75 (1H, m), and 1.42 (6H, d, J 7.5 Hz).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was evaporated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluting with hexane/EtOAc (90:10)

出典と根拠

ORDレコード
ord-636b5bf3265446f7bd753568e9000839
出典データセット
uspto-grants-2000_06
特許番号
US06071927

反応ノート

読み込み中…