Catechol → o-(5-Fluoro-2-nitrophenoxy)phenol

HRID 21520

반응식

HRID 21520 반응식
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>C(#N)C.[Cl-].[Na+].O.C(Cl)Cl>[F:22][C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([CH:21]=1)[O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

참가 물질

7

반응물 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

생성물 1

HCID 19932387o-(5-Fluoro-2-nitrophenoxy)phenol수율 55%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
28 °C

실험 절차

Catechol (103.8 g, 0.94 mol) and potassium carbonate (129.9 g, 0.94 mol) are added to a solution of 2,4-difluoronitrobenzene (50.0 g, 0.314 mol) in acetonitrile. The reaction mixture is stirred at 28° C. for 24 hours, poured into brine and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown gum. Flash chromatography of the gum using silica gel and a 10% hexanes in methylene chloride solution gives the title product as a yellow solid (43 g) which is identified by 1HNMR spectral analysis.

후처리

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washis washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a brown gum

출처 및 근거

ORD 기록
ord-3ac0287e59ea458f9d86f75740575bec
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424280

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