O-Xylene → 1-Chloro-2-fluoro-3-nitrobenzene

HRID 2260450Notes

Reaction equation

HRID 2260450 reaction equation
[F-:1].[K+].Cl[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].C1(C)C(C)=CC=CC=1>>[Cl:10][C:9]1[C:4]([F:1])=[C:5]([N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 185552,3-DichloronitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 750161-Chloro-2-fluoro-3-nitrobenzene

Conditions

Temperature
150 °C

Procedure

In a 1-liter flange flask fitted with a distillation bridge and stirrer, 139 g (2.4 mol) of potassium fluoride were introduced at 120° C. into the melt of 576 g (3.0 mol) of 2,3-dichloronitrobenzene. Subsequently, 20 g (0.19 mol) of xylene were added and the reaction suspension was azeotropically dried by application of a vacuum of 60 mbar and heating to 150° C. After the xylene had been distilled off, the distillation bridge was replaced by a reflux condenser, the reaction suspension was heated to 190° C. and stirred for 6 hours at this temperature. Amount of 3-chloro-2-fluoronitrobenzene formed: 0.5 GC area-% after 6 hours.

Workup

  1. customthe reaction suspension was azeotropically dried by application of a vacuum of 60 mbar
  2. distillationAfter the xylene had been distilled off
  3. customthe distillation bridge was replaced by a reflux condenser
  4. temperaturethe reaction suspension was heated to 190° C.

Sources & evidence

ORD record
ord-32a1044ad7504c3fbbcd6d7fd1a5086e
Source dataset
uspto-grants-1995_12
Patent number
US05476976

Reaction notes

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