1,2-Dichloroethane → Pentachlorofluorobenzene

HRID 736962Notes

Reaction equation

HRID 736962 reaction equation
[F:1][C:2]1C=C[CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-:9].[Cl-:10].[Cl-:11].ClCl.O.[Cl:15][CH2:16][CH2:17][Cl:18]>>[Cl:15][C:16]1[C:2]([F:1])=[C:3]([Cl:9])[C:4]([Cl:10])=[C:5]([Cl:11])[C:17]=1[Cl:18]

Participants

6

Conditions

Temperature
25 °C

Procedure

A solution of 144 g (1.5 mol) of fluorobenzene in 1080 ml of 1,2-dichloroethane was admixed with 10 g (0.075 mol) of powdered AlCl3, and 586 g of chlorine gas were then passed into the mixture at 5-15° C. The solution was then stirred at 25° C. for about 5 hours, then heated to 65° C. and 100 ml of water were subsequently added while stirring vigorously. At this temperature, the phases were separated and the organic phase was extracted with water. The solvent was distilled off and the residue was taken up in 1300 g of NMP. After gas-chromatographic analysis (GC), the yield was calculated as: 93.9% of pentachlorofluorobenzene, 4.9% of hexachlorobenzene and 1.1% of tetrachlorofluorobenzenes. The solution can directly be reacted further as described in example 6.

Workup

  1. customwere then passed into the mixture at 5-15° C
  2. temperatureheated to 65° C.
  3. stirringwhile stirring vigorously
  4. customAt this temperature, the phases were separated
  5. extractionthe organic phase was extracted with water
  6. distillationThe solvent was distilled off
  7. customThe solution can directly be reacted further

Sources & evidence

ORD record
ord-7daf14fb73924d3b973634c13427808d
Source dataset
uspto-grants-2009_09
Patent number
US07595426B2

Reaction notes

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