Ammonium Chloride → 3-Bromo-5-(difluoromethyl)aniline

HRID 1040031노트

반응식

HRID 1040031 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH:11]([F:13])[F:12])[CH:3]=1.[NH4+].[Cl-]>C(O)C.O.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH:11]([F:12])[F:13])[CH:3]=1)[NH2:8]

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 672481711-Bromo-3-(difluoromethyl)-5-nitrobenzene

생성물 1

HCID 584563863-Bromo-5-(difluoromethyl)aniline수율 82.1%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
95 °C

실험 절차

Iron (1.99 g, 35.7 mmol) was added to a vigorously stirred mixture of 1-bromo-3-(difluoromethyl)-5-nitrobenzene (1.80 g, 7.14 mmol) and NH4Cl (0.191 g, 3.57 mmol) in ethanol (30 mL) and water (15 mL). The mixture was heated to 95° C. for 2 h. It was then diluted with ethyl acetate while still hot and filtered over Celite. The filtrate was washed with dilute aqueous NaHCO3 and brine. After solvent evaporation the residue was purified through a silica plug, eluting with 1:5 ethyl acetate:hexanes to yield 3-bromo-5-(difluoromethyl)aniline (1.3 g, 5.86 mmol, 82%).

후처리

  1. filtrationfiltered over Celite
  2. washThe filtrate was washed with dilute aqueous NaHCO3 and brine
  3. customAfter solvent evaporation the residue
  4. customwas purified through a silica plug
  5. washeluting with 1:5 ethyl acetate

출처 및 근거

ORD 기록
ord-42645d21227d45138c896c2aef8ff410
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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