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

HRID 21520

Reaction equation

HRID 21520 reaction equation
[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]

Participants

7

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

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

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
28 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ac0287e59ea458f9d86f75740575bec
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Linked notes

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