4-Fluorophenol → HCID 14425969, compound

HRID 1196628Notes

Reaction equation

HRID 1196628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+]([C:18]1[CH:19]=[C:20]([CH3:25])[N+:21]([O-:24])=[CH:22][CH:23]=1)([O-])=O>CN(C)C(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:18]2[CH:19]=[C:20]([CH3:25])[N+:21]([O-:24])=[CH:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium Carbonate2×HCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

Product 1

HCID 14425969HCID 14425969, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
80 °C

Procedure

6.2 g (55 mmol) of 4-fluorophenol are dissolved in 75 ml of N,N-dimethylacetamide and 20.7 g (150 mmol) of finely powdered potassium carbonate was added. 7.7 g (50 mmol) of 4-nitro-2-picoline-N-oxide are added to this suspension and the mixture is warmed at 80° C. for 3 hours. A further 7 g (50 mmol) of potassium carbonate are subsequently added and the mixture is stirred for one hour at 100° C. After cooling, it is freed from N,N-dimethylacetamide in vacuo, and the residue is taken up in water, extracted a number of times using dichloromethane, dried over MgSO4 and concentrated, and the residue is brought to crystallization using diisopropyl ether, m.p. 122°-124° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted a number of times
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customthe residue is brought to crystallization

Sources & evidence

ORD record
ord-0735a2f043324f18a7df9e8b4d5e2eb0
Source dataset
uspto-grants-1992_05
Patent number
US05114955

Reaction notes

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