1,2-Dichloro-4-nitrobenzene → 2-Chloro-1-fluoro-4-nitrobenzene

HRID 903125Notes

Reaction equation

HRID 903125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[F-:12].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:12]

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 2855718-Crown-6HCID 522689Potassium Fluoride

Product 1

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1,500 parts of 3,4-dichloronitrobenzene, 680 parts of potassium fluoride and 25 parts of 18-crown-6 in 1,420 parts of dimethylformamide is refluxed for 9 hours, the temperature being 165° C. The mixture is worked up by the method described in Example 1. 1,124 parts (82% of theory) of 3-chloro-4-fluoronitrobenzene of melting point 41°-42° C. are obtained.

Workup

  1. temperatureis refluxed for 9 hours
  2. custombeing 165° C

Sources & evidence

ORD record
ord-ee91f6a7037544edb03b71fce09d366a
Source dataset
uspto-grants-1980_10
Patent number
US04226811

Reaction notes

Loading…