1-Bromo-2,4-difluoro-5-nitrobenzene → 5-Bromo-2,4-difluoroaniline

HRID 1269173ノート

反応式

HRID 1269173 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[F:12]>CCO.C1COCC1.[NH4+].[Cl-].O.[Fe]>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:7]=1)[NH2:8]

参加物

7

反応物 1

HCID 2230781-Bromo-2,4-difluoro-5-nitrobenzene

生成物 1

HCID 27832955-Bromo-2,4-difluoroaniline収率 59%

試薬・触媒・溶媒 5

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of 1-bromo-2,4-difluoro-5-nitrobenzene (5.04 g, 21.3 mmol) in EtOH (100 mL), THF (50 mL), NH4Cl (sat) (25 mL) and H2O (25 mL) was added iron powder (5.0 g, 89.5 mmol). The mixture was refluxed for 2 h and filtered through celite. The filter pad was washed with EtOAc (3×50 mL). The filtrate was concentrated and the residue was partitioned between EtOAc and brine. The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography (5–10% EtOAc/Hexane) provided 2.6 g (59%) of 5-bromo-2,4-difluoroaniline: ESMS m/e: 208.2 (M+H)+.

後処理

  1. temperatureThe mixture was refluxed for 2 h
  2. filtrationfiltered through celite
  3. washThe filter pad was washed with EtOAc (3×50 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between EtOAc and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customPurification by flash chromatography (5–10% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-0e7abc628b9b4e7d9322d41c78b028ac
出典データセット
uspto-grants-2007_04
特許番号
US07199135B2

反応ノート

読み込み中…