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

HRID 2211349Notes

Reaction equation

HRID 2211349 reaction equation
[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCCCC.[Cl:24][C:25]1[CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31].ClC1C=CC=CC=1C.[F-:43].[K+]>>[Cl:24][C:25]1[CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[CH:29][C:30]=1[F:43].[Cl:24][C:25]1[CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

6

Reactant 4

HCID 72382-ChlorotolueneHCID 74431,2-Dichloro-4-nitrobenzeneHCID 8155Stearyltrimethylammonium chlorideHCID 522689Potassium Fluoride

Product 2

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 79%

Conditions

Temperature
180 °C

Procedure

100 g of octadecyltrimethylammonium chloride are dissolved at 60° C. in 2900 g (15.1 mol) of 3,4-dichloronitrobenzene. 100 g of 2-chlorotoluene are added to the solution. After addition of 825 g (14.2 mol) of potassium fluoride, the resulting suspension is heated for 11 hours at 180° 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 1966 g (79% of theory) of 3-chloro-4-fluoronitrobenzene and 340 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-3df9ec8c0d1444d6a421c39835a817b6
Source dataset
uspto-grants-1995_10
Patent number
US05463148

Reaction notes

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