2-Chlorotoluene → 2-Chloro-1-fluoro-4-nitrobenzene

HRID 2211352Notes

Reaction equation

HRID 2211352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=CC=CC=1C.[F-:20].[K+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:20].[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 72382-ChlorotolueneHCID 74431,2-Dichloro-4-nitrobenzeneHCID 522689Potassium Fluoride

Product 2

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 84716Hexadecyltributylphosphonium bromideCatalyst

Conditions

Temperature
200 °C

Procedure

25 g of hexadecyltributylphosphonium bromide are dissolved at 60° C. in 1010 g (5.25 mol) of 3,4-dichloronitrobenzene. 100 g of 2-chlorotoluene are added to the solution. After addition of 290 g (5.0 mol) of potassium fluoride, the resulting suspension is heated for 16 h at 200° C. 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, 711 g (81% of theory) of 3-chloro-4-fluoronitrobenzene and 115 g of unreacted 3,4-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-7bbcb89743964412abf86920d1ffc0b7
Source dataset
uspto-grants-1995_10
Patent number
US05463148

Reaction notes

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