4,5-Dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane → 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole

HRID 259847Notes

Reaction equation

HRID 259847 reaction equation
[Mg].Cl[C:3]1([F:18])[C:7]([F:9])(Cl)[O:6][C:5]([C:14]([F:17])([F:16])[F:15])([C:10]([F:13])([F:12])[F:11])[O:4]1>BrBr.O1CCCC1>[F:9][C:7]1[O:6][C:5]([C:14]([F:15])([F:16])[F:17])([C:10]([F:11])([F:13])[F:12])[O:4][C:3]=1[F:18]

Participants

5

Reactant 2

HCID 1629194,5-Dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolaneHCID 5462224Magnesium

Product 1

HCID 1699574,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxoleYield 57.2%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
28 °C

Procedure

A solution of bromine (3 g) and tetrahydrofuran (30 mL) was slowly added to a well stirred mixture of magnesium turnings (25 g) and tetrahydrofuran (365 mL) at 20° C. After the exothermic reaction stopped, the reaction mixture was cooled to 28° C. and 133 g of the 4,5-dichloro-perfluoro-2,2-dimethyl-1,3-dioxolane (89.9% trans and 10.1% cis) was slowly added. After an induction period an exothermic reaction was observed. The reaction mixture was distilled to remove all material boiling up to 65° C. The distillate was washed with ice water to give 58.9 g perfluoro-2,2-dimethyl-1,3-dioxole.

Workup

  1. customAfter the exothermic reaction
  2. customAfter an induction period an exothermic reaction
  3. distillationThe reaction mixture was distilled
  4. customto remove all material
  5. customboiling up to 65° C
  6. washThe distillate was washed with ice water

Sources & evidence

ORD record
ord-df2c2bff764f4fd8bff74a61a2e6fbf2
Source dataset
uspto-grants-1996_06
Patent number
US05523422

Reaction notes

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