1,3-Difluorobenzene → 1,2,3,5-Tetrachloro-4,6-difluorobenzene

HRID 736961Notes

Reaction equation

HRID 736961 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Al+3].[Cl-:10].[Cl-:11].[Cl-:12].[Cl:13]Cl>ClCCCl>[F:1][C:2]1[C:7]([Cl:10])=[C:6]([Cl:11])[C:5]([Cl:12])=[C:4]([F:8])[C:3]=1[Cl:13]

Participants

5

Reactant 3

HCID 97411,3-DifluorobenzeneHCID 24526ChlorineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6199151,2,3,5-Tetrachloro-4,6-difluorobenzene

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 100 g (0.88 mol) of 1,3-difluorobenzene in 1 l of 1,2-dichloroethane was admixed with 11.7 g (0.088 mol) of powdered AlCl3. 290 g of chlorine gas were subsequently passed into the solution at 0-5° C. After the end of the reaction, the HCl formed were driven out at about 20-25° C. by means of a stream of nitrogen, and the solution was filtered through silica gel. According to analysis by gas chromatography, the solution comprised 38.5% of dichlorodifluorobenzene, 33.6% of difluorotrichlorobenzenes, 14.5% of difluorotetrachlorobenzene as main components and also further components in the percentage range. A vacuum distillation gave, at 0.2 mbar in the temperature range 50-90° C., 60 g of a fraction comprising the title compound.

Workup

  1. customwere subsequently passed into the solution at 0-5° C
  2. customAfter the end of the reaction

Sources & evidence

ORD record
ord-746f8c90c0c14250827b7125850b91b6
Source dataset
uspto-grants-2009_09
Patent number
US07595426B2

Reaction notes

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