1-Chloro-4-nitrobenzene → p-Fluoronitrobenzene

HRID 1074324Notes

Reaction equation

HRID 1074324 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F-:11].[K+]>S1(CCCC1)(=O)=O.[Cl-].C([N+]1C=CC(N(CCCC)CCCC)=CC=1)C(C)(C)C>[F:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 74741-Chloro-4-nitrobenzene2×HCID 522689Potassium Fluoride

Product 1

HCID 9590p-FluoronitrobenzeneYield 96.3%

Reagents, catalysts & solvents 2

HCID 13306852HCID 13306852, compoundCatalystHCID 31347SulfolaneSolvent

Procedure

A reaction mixture of 85.3 g of 4-chloronitrobenzene (CNB), 45.3 g of potassium fluoride, 1.4 g of the N-neopentyl-4-(N',-N'-di-n-butylamino)pyridinium chloride (NPDBAPC) obtained in Example lII in 109.6 g of sulfolane was heated with stirring for 9 hours at 205°-215° C. At the end of this period, HPLC assay of a sample of the reaction mixture indicated less than 1% residual CNB. Simple distillation of the reaction mixture under vacuum gave 73.6 g of 4-fluoronitrobenzene (FNB) for a 96.3% yield.

Workup

  1. temperaturewas heated
  2. distillationSimple distillation of the reaction mixture under vacuum

Sources & evidence

ORD record
ord-aeaf7bb70e374d6e8e8a31961025304d
Source dataset
uspto-grants-1990_11
Patent number
US04973772

Reaction notes

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