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

HRID 1111195Notes

Reaction equation

HRID 1111195 reaction equation
[F-:1].[K+].C1S(=O)(=O)CCC1.[Cl:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][C:16]=1Cl>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[Al+3].[Cl-].[Cl-].[Cl-]>[Cl:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[CH:15][C:16]=1[F:1]

Participants

6

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 31347SulfolaneHCID 522689Potassium Fluoride

Product 1

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 85%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6451240Aluminum(III) ChlorideCatalyst

Procedure

A mixture of 87 g (1.5 mol) of potassium fluoride and 250 g of tetramethylene sulphone in a glass reaction vessel was subjected to incipient distillation for the removal of water until 25 g of tetramethylene sulphone had passed over. 192 g of 3,4-dichloro-nitrobenzene, 10 g (0.025 mol) of methyl -trioctyl-ammonium chloride and 1.65 g (0.0125 mol) of AlCl3 were then added and the was 97% (determined by gas chromatography). The reaction mixture was then worked up by distillation. 149 g of 3-chloro-4-fluoro-nitrobenzene having a boiling point of 92°-93° C. at 10 mbar were obtained. This corresponds to a yield of 85% of theory.

Workup

  1. customin a glass reaction vessel
  2. distillationwas subjected to incipient distillation for the removal of water until 25 g of tetramethylene sulphone
  3. distillationThe reaction mixture was then worked up by distillation

Sources & evidence

ORD record
ord-29670d8167bf49e9b9da38faa843f08f
Source dataset
uspto-grants-1990_12
Patent number
US04978769

Reaction notes

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