Nitrogen → 4-(4-Fluorophenoxy)-1-methyl-2-nitrobenzene

HRID 263436

Reaction equation

HRID 263436 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].N#N>CCOCC.N1C=CC=CC=1>[N+:9]([C:4]1[CH:3]=[C:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[CH3:8])([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 947NitrogenHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 1235464-Bromo-2-nitrotoluene

Product 1

HCID 35376734-(4-Fluorophenoxy)-1-methyl-2-nitrobenzeneYield 63.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-2-nitrotoluene (25.0g, 116 mmol), 4-fluorophenol (8.70g, 77.6 mmol), potassium carbonate (21.5g, 156 mmol) and pyridine (75 mL), were combined under N2 atmosphere and heated at 90° C. for 30 min. The reaction mixture was cooled to ambient temperature, CuO (15.4g, 194 mmol) was added under a stream of N2, and the resulting dark-brown suspension was heated at reflux for 17 hours. The reaction mixture was cooled to ambient temperature and diluted with ether. The solids were removed by filtration through celite. The ethereal solution was washed with 1.0M aqueous NaOH, 1.0M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a dark-brown oil. The crude product was purified by chromatography on silica gel to give 2-nitro-4-(4-fluorophenoxy)-toluene (12.1 g, 63%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. temperaturethe resulting dark-brown suspension was heated
  3. temperatureat reflux for 17 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. customThe solids were removed by filtration through celite
  6. washThe ethereal solution was washed with 1.0M aqueous NaOH, 1.0M aqueous HCl and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a dark-brown oil
  11. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2111e3ecfd044200b27d59782b961da2
Source dataset
uspto-grants-1997_07
Patent number
US05643922

Linked notes

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