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

HRID 1577352Notes

Reaction equation

HRID 1577352 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]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[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 41%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
140 °C

Procedure

Potassium fluoride (69.6 g; 1.2 mole) and benzyltriethylammonium chloride (10.7 g; 0.05 mole) were added to molten 2-chloronitrobenzene (157.5 g; 1.0 mole). After stirring at 140° C. for 28 hours and a similar work-up to Example 1, 2-fluoronitrobenzene was obtained in 41% yield together with 7% recovered 2-chloronitrobenzene.

Sources & evidence

ORD record
ord-9eb23bd186f740f7924861d12176e845
Source dataset
uspto-grants-1981_09
Patent number
US04287374

Reaction notes

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