Ethyl Acetate → 5-Chloro-4'-fluorobiphenyl-2-amine

HRID 238957노트

반응식

HRID 238957 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 674497455-Chloro-4'-fluoro-2-nitrobiphenyl

생성물 1

HCID 584829885-Chloro-4'-fluorobiphenyl-2-amine수율 70.1%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a solution of the above 5-chloro-4′-fluoro-2-nitrobiphenyl (4.20 g, 15.7 mmol) and iron powder (2.75 g, 49.3 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), it was dried with sodium sulfate. After the filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3, v/v) to give the title compound (2.43 g, 11.0 mmol, 67%).

후처리

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washAfter the organic phase was washed with water (30 mL), it
  4. dry with materialwas dried with sodium sulfate
  5. filtrationAfter the filtration and concentration
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3

출처 및 근거

ORD 기록
ord-40d71a0d48274ca1b68444f92e9bd1e1
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642640B2

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