1-Chloro-2-nitrobenzene → 1-Fluoro-2-nitrobenzene

HRID 903813Notes

Reaction equation

HRID 903813 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F-:11].[K+].[F-].[Cs+].C1S(=O)(=O)CCC1>>[F:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 69451-Chloro-2-nitrobenzeneHCID 25953Cesium fluorideHCID 31347SulfolaneHCID 522689Potassium Fluoride

Product 1

HCID 738951-Fluoro-2-nitrobenzeneYield 85.5%

Conditions

Temperature
110 °C

Procedure

1,300 parts of o-chloronitrobenzene, 960 parts of potassium fluoride and 25 parts of cesium fluoride are stirred in 1,300 parts of tetramethylenesulfone under nitrogen for 16 hours at 225° 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. 991 parts (85.5% of theory) of o-fluoronitrobenzene of boiling point 55° to 57° C/1.2 mm Hg are obtained.

Workup

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

Sources & evidence

ORD record
ord-8452dcd2f2e648ac9eac119d3f72f2d4
Source dataset
uspto-grants-1980_10
Patent number
US04229365

Reaction notes

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