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

HRID 1420691ノート

反応式

HRID 1420691 の反応式
I[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[OH:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:2]([O:15][C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[Br:5])([CH3:4])[CH3:3]

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

2-Iodopropane (2.2 g) was added to a mixture of 2-bromo-4-nitrophenol (2.5 g) and potassium carbonate (5 g) in acetone (30 ml) and the mixture heated under reflux for 18 hours. The mixture was cooled and 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 evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/EtOAc (90:10), to give the title compound (2.8 g, 94%); δH (250MHz, CDCl3) 1.42 (6H, d, J 5.7Hz, OCH(CH3)2), 4.75 (1H, m, OCH(CH3)2), 6.93 (1H, m, ArH), 8.20 (1H, m, ArH), 8.46 (1H, s, ArH).

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue was purified by flash chromatography
  11. washeluting with hexane/EtOAc (90:10)

出典と根拠

ORDレコード
ord-4e68f1bffda14a7cb4c98afd65ba0ef6
出典データセット
uspto-grants-2000_06
特許番号
US06071928

反応ノート

読み込み中…