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

HRID 1577353Notes

Reaction equation

HRID 1577353 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]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC>[F:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 738951-Fluoro-2-nitrobenzeneYield 91.2%

Reagents, catalysts & solvents 1

HCID 84716Hexadecyltributylphosphonium bromideCatalyst

Conditions

Temperature
145 °C

Procedure

Potassium fluoride (69.6 g; 1.2 mole) and hexadecyltributylphosphonium bromide (25.2 g; 0.04 mole) were added to molten 2-chloronitrobenzene (157.5 g; 1 mole). After stirring at 145° C. for 24 hours and a similar work-up to Example 1, 2-fluoronitrobenzene was obtained in 91.2% yield together with 2.4% recovered 2-chloronitrobenzene.

Sources & evidence

ORD record
ord-6d514da159824f18893126a302b97b0c
Source dataset
uspto-grants-1981_09
Patent number
US04287374

Reaction notes

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