Sulfolane → 1,2-Difluoro-4-nitrobenzene

HRID 903817Notes

Reaction equation

HRID 903817 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[F-:12].[K+].C1S(=O)(=O)CCC1>>[F:12][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 1230531,2-Difluoro-4-nitrobenzeneYield 10.3%

Conditions

Temperature
110 °C

Procedure

1,500 parts of 3-chloro-4-fluoronitrobenzene and 1,000 parts of potassium fluoride are heated in 1,500 parts of tetramethylenesulfone for 16 hours at 230° C. The solution is cooled to 110° C. and filtered, the solid residue is washed with 500 parts of methylene chloride and the filtrates are combined and distilled. 139 parts (10.3% of theory) of 3,4-difluoronitrobenzene of boiling point 54° C./1 mbar are obtained.

Workup

  1. filtrationfiltered
  2. washthe solid residue is washed with 500 parts of methylene chloride
  3. distillationdistilled

Sources & evidence

ORD record
ord-ece6c8cbb1004dac84d1b9ec8f1ef522
Source dataset
uspto-grants-1980_10
Patent number
US04229365

Reaction notes

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