Chlorine → 1,5-Dichloro-2,4-difluorobenzene

HRID 487373Notes

Reaction equation

HRID 487373 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([N+]([O-])=O)[CH:7]=1.[Cl:13]Cl>[Fe]>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([Cl:13])[CH:7]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 738671-Chloro-2,4-difluoro-5-nitrobenzene

Product 1

HCID 109541771,5-Dichloro-2,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
200 °C

Procedure

3 kg (15.5 mol) of iron-free, dry 5-chloro-2,4-difluoronitrobenzene are introduced into a 2 l four-necked flask with stirrer, dropping funnel and gas inlet tube and, on top, a column with reflux condenser. After heating the reaction solution to 200° C., chlorine is passed through the solution at a rate of 15 l/h. After 4-6 hours, the solution begins to boil, and after a further 2-4 hours the 1,3-dichloro-4,6-difluorobenzene which is formed can be taken off at the head of the column. At the same time, fresh 5-chloro-2,4-difluoronitrobenzene is added to the reaction in accordance with the quantity of product removed.

Workup

  1. temperatureon top, a column with reflux condenser

Sources & evidence

ORD record
ord-e251f72237e24c3bbe9548a850d1532f
Source dataset
uspto-grants-1994_03
Patent number
US05294742

Reaction notes

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