Vinylidene chloride → 4-Bromo-3-chloro-3,4,4-trifluorobutanoic acid

HRID 940

Reaction equation

HRID 940 reaction equation
[Cl:1][C:2]([F:8])(Br)[C:3]([F:6])([F:5])[Br:4].[Cl:9][C:10]([F:16])(Cl)[C:11]([F:14])([F:13])[Cl:12].[C:17](Cl)(Cl)=C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[CH:31]([O-:33])=[O:32].[Na+]>CN(C=O)C>[Br:4][C:3]([F:6])([F:5])[C:2]([Cl:1])([F:8])[CH2:10][C:31]([OH:33])=[O:32].[Cl:9][C:10]([F:16])([C:11]([Cl:12])([F:14])[F:13])[CH2:17][C:31]([OH:33])=[O:32]

Participants

7

Reactant 4

HCID 6366Vinylidene chlorideHCID 6428Cfc 113HCID 96341,2-Dibromo-1-chloro-1,2,2-trifluoroethaneHCID 86752166Persulfate sodium formate

Product 2

HCID 109121274-Bromo-3-chloro-3,4,4-trifluorobutanoic acidHCID 218364853,4-Dichloro-3,4,4-trifluorobutanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) or 1,1,2-trichlorotrifiuoroethane (X) with vinylidene chloride in the presence of ammoninm persulfate/sodium formate/air in DMF to give 4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid (VIII) or 3,4- dichloro-3,4,4-trifluorobutanoic acid (XI).

Sources & evidence

ORD record
ord-785f3c16cc454b2f8882766f14740ddd
Source dataset
uspto-grants-1998_03
Patent number
US05723470

Linked notes

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