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

HRID 1269173노트

반응식

HRID 1269173 반응식
[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]

참가 물질

7

반응물 1

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

생성물 1

HCID 27832955-Bromo-2,4-difluoroaniline수율 59%

시약·촉매·용매 5

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0e7abc628b9b4e7d9322d41c78b028ac
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199135B2

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