1-Chloro-2-nitrobenzene → Sulfolane

HRID 903124Notes

Reaction equation

HRID 903124 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+].C1OCCOCCOCCOCCOCCOC1.[CH2:31]1[S:35](=[O:37])(=[O:36])[CH2:34][CH2:33][CH2:32]1>>[F:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:34]1[S:35](=[O:37])(=[O:36])[CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 69451-Chloro-2-nitrobenzeneHCID 2855718-Crown-6HCID 31347SulfolaneHCID 522689Potassium Fluoride

Product 2

HCID 31347SulfolaneYield 99.2%HCID 738951-Fluoro-2-nitrobenzeneYield 80%

Conditions

Temperature
110 °C

Procedure

1,300 parts of o-chloronitrobenzene, 960 parts of potassium fluoride and 82.5 parts of 18-crown-6 in 1,300 parts of tetramethylenesulfone are stirred under nitrogen for 30 hours at 180° C. The solution is cooled to 110° C. and filtered, the solid residue is rinsed with 500 parts of methylene chloride and the filtrates are combined and distilled. 932 parts (80% of theory) of o-fluoronitrobenzene of boiling point 55°-57° C./1.2 mm Hg and 1,290 parts (99.2% of theory) of tetramethylenesulfone of boiling point 105°-110° C. are obtained. About 70% of the crown ether can be recovered from the distillation residue by repeated extraction by shaking with water.

Workup

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

Sources & evidence

ORD record
ord-dd4c57d8d6fb4c5da8b1705a2886490f
Source dataset
uspto-grants-1980_10
Patent number
US04226811

Reaction notes

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