Dinitrofluorobenzene → HCID 2801602, compound

HRID 329914Notes

Reaction equation

HRID 329914 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[C:20]1([S:26][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 2801602HCID 2801602, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 2,4-dinitrofluorobenzene, 5.69 ml (45 mmol) and potassium carbonate 6.3 g (45 mmol) in acetone was added benzenethiol 4.65 ml (45 mmol). The mixture was heated to reflux for 2 hours, cooled and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated potassium carbonate, dried over sodium sulfate, filtered and the solvent removed under reduced pressure to give 7.0 g (56%) of 2,4-dinitrophenyl phenyl sulfide.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with saturated potassium carbonate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7183ce110e0240da89ef8b7d0565f938
Source dataset
uspto-grants-1990_01
Patent number
US04894358

Reaction notes

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