1-Chloro-2-nitrobenzene → 1-Fluoro-2-nitrobenzene

HRID 1577356Notes

Reaction equation

[F-:1].[K+].Cl[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].S1(CCCC1)(=O)=O>>[F:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

Reactant 3

HCID 69451-Chloro-2-nitrobenzene

HCID 31347Sulfolane

HCID 522689Potassium Fluoride

Product 1

HCID 738951-Fluoro-2-nitrobenzeneYield 16%

Conditions

Temperature: 140 °C

Procedure

A mixture of potassium fluoride (61.5 g; 1.06 mole), 2-chloronitrobenzene (157.5 g; 1.0 mole) and sulpholane (88.8 g; 0.74 mole) was heated to 140° C. for 28 hours. 2-Fluoronitrobenzene was obtained in 16% yield together with 61% recovered 2-chloronitrobenzene.

Sources & evidence

ORD record: ord-5676c2808bb84e499f5bdc45371affcc
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04287374

Reaction notes

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