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

HRID 1577351Notes

Reaction equation

HRID 1577351 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([N+](C)(C)C)CCCCCCCCCCCCC>[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 78%

Reagents, catalysts & solvents 1

HCID 14250Tetradecyltrimethylammonium bromideCatalyst

Conditions

Temperature
140 °C

Procedure

Potassium fluoride (water content 0.2%) (69.6 g; 1.2 mole) and tetradecyltrimethylammonium bromide (18 g; 0.055 mole) were added to molten 2-chloronitrobenzene (157.5 g; 1 mole) with stirring. The mixture was heated to 140° C. for 28 hours. The reaction mixture was then allowed to cool to c. 100° C. and was filtered with the assistance of added toluene. The toluene was distilled and the residue was finally distilled in high vacuum to give 2-fluoronitrobenzene in 78% yield together with 5% recovered 2-chloronitrobenzene.

Workup

  1. temperatureto cool to c
  2. filtration100° C. and was filtered with the assistance of added toluene
  3. distillationThe toluene was distilled
  4. distillationthe residue was finally distilled in high vacuum

Sources & evidence

ORD record
ord-22b9820c5e5a46e29fab0731b3a5c991
Source dataset
uspto-grants-1981_09
Patent number
US04287374

Reaction notes

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