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

HRID 2260456Notes

Reaction equation

HRID 2260456 reaction equation
[F-:1].[K+].[Cl-].[NH4+].[Cl:5][C:6]1[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][C:11]=1Cl>C1(C)C(C)=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][C:11]=1[F:1]

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 25517Ammonium ChlorideHCID 522689Potassium Fluoride

Product 1

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 71%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneCatalyst

Procedure

In a 1-liter flange flask fitted with a distillation bridge and impeller stirrer, 240 g (4.1 mol) of potassium fluoride, 30 g (0.05 mol) of dimethyldi (ethoxypolyoxypropyl methyl ether)ammonium chloride and 30 g of xylene were introduced at 70° C. into the melt of 767 g (4.0 mol) of 3,4-dichloronitrobenzene, and the reaction suspension was azeotropically dried under reduced pressure up to 120° C. 498 g (2.84 mol) of 3-chloro-4-fluoronitrobenzene were isolated. Amount of 3-chloro-4-fluoronitrobenzene formed, according to GC analysis:

Workup

  1. customthe reaction suspension was azeotropically dried under reduced pressure up to 120° C

Sources & evidence

ORD record
ord-6080ea679795486bbaedbe920afdff5f
Source dataset
uspto-grants-1995_12
Patent number
US05476976

Reaction notes

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