2,3-Dichloronitrobenzene → 1-Chloro-2-fluoro-3-nitrobenzene

HRID 2211351Notes

Reaction equation

HRID 2211351 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F-:12].[K+]>[Cl-].C[N+](C)(C)C.ClC1C=CC=CC=1C>[F:12][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 2

HCID 185552,3-DichloronitrobenzeneHCID 522689Potassium Fluoride

Product 2

HCID 185552,3-DichloronitrobenzeneHCID 750161-Chloro-2-fluoro-3-nitrobenzeneYield 57%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 72382-ChlorotolueneSolvent

Conditions

Temperature
180 °C

Procedure

20 g of tetramethylammonium chloride are dissolved at 70° C. in 100 g of 2-chlorotoluene. 1230 g (6.5 mol) of 2,3-dichloronitrobenzene are added to the solution. After addition of 290 g (5 mol) of potassium fluoride, the resulting suspension is heated for 14 hours at 180° C. with stirring and under nitrogen. During this time, some of the 2-chlorotoluene is continuously distilled off. The reaction suspension is then quickly filtered off using suction, the filter cake is washed with 2-chlorotoluene and the combined filtrates are fractionated in vacuo. In this manner 505 g (57% of theory) of 2-fluoro-3-chloronitrobenzene and 437 g of unreacted 2,3-dichloronitrobenzene are obtained.

Workup

  1. distillationDuring this time, some of the 2-chlorotoluene is continuously distilled off
  2. filtrationThe reaction suspension is then quickly filtered off
  3. washthe filter cake is washed with 2-chlorotoluene

Sources & evidence

ORD record
ord-97b06da1c5514897b3c3b0ea2cd3f0cf
Source dataset
uspto-grants-1995_10
Patent number
US05463148

Reaction notes

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