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

HRID 903814Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[F-:12].[K+].[F-].[Cs+].C1S(=O)(=O)CCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:12]

Participants

Reactant 4

HCID 74431,2-Dichloro-4-nitrobenzene

HCID 25953Cesium fluoride

HCID 31347Sulfolane

HCID 522689Potassium Fluoride

Product 1

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 93%

Procedure

1,500 parts of 3,4-dichloronitrobenzene, 680 parts of potassium fluoride and 5 parts of cesium fluoride are stirred in 1,500 parts of tetramethylenesulfone under nitrogen for 3 hours at 220° C. Working up takes place as described in Example 1(a). 1,275 parts (93% of theory) of 3-chloro-4-fluoronitrobenzene of melting point 41°-42° C. are obtained.

Sources & evidence

ORD record: ord-54ce1f86f54c48cc9dfab5c428c9a694
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04229365

Reaction notes

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