Reaction #1036

ord-785f3c16cc454b2f8882766f14740ddd

Reaction equation

FC(F)(Br)C(F)(Cl)Br
1-chloro-1,2-dibromotrifluoroethane
FC(F)(Cl)C(F)(Cl)Cl
1,1,2-trichlorotrifiuoroethane
C=C(Cl)Cl
vinylidene chloride
O=C[O-].O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+]
persulfate sodium formate
→
O=C(O)CC(F)(Cl)C(F)(F)Br
4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid
O=C(O)CC(F)(Cl)C(F)(F)Cl
3,4- dichloro-3,4,4-trifluorobutanoic acid

Reactants

FC(F)(Br)C(F)(Cl)Br
1-chloro-1,2-dibromotrifluoroethane
FC(F)(Cl)C(F)(Cl)Cl
1,1,2-trichlorotrifiuoroethane
C=C(Cl)Cl
vinylidene chloride
O=C[O-].O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+]
persulfate sodium formate

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723470uspto-grants-1998_03