Ethyl vinyl ether → 4-Bromo-3-chloro-3,4,4-trifluorobutanoic acid

Reaction equation

ClC(F)(Br)C(F)(F)Br.C(OCC)=C.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:22](=[O:25])(O)[O-:23].[Na+].[Br:27][C:28]([F:36])([F:35])[C:29]([Cl:34])([F:33])[CH2:30]C=O.Cl([O-])=O.[Na+].OO>>[Br:27][C:28]([F:36])([F:35])[C:29]([Cl:34])([F:33])[CH2:30][C:22]([OH:23])=[O:25]

Participants

Reactant 5

HCID 8023Ethyl vinyl ether

HCID 96341,2-Dibromo-1-chloro-1,2,2-trifluoroethane

HCID 218364804-Bromo-3-chloro-3,4,4-trifluorobutanal

HCID 86632281Sodium chlorite hydrogen peroxide

HCID 86749472Sodium hydrosulfite sodium bicarbonate

Product 1

HCID 109121274-Bromo-3-chloro-3,4,4-trifluorobutanoic acid

Procedure

A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) with ethyl vinyl ether in the presence of sodium hydrosulfite/sodium bicarbonate followed by oxidation of the intermediate, 4-bromo-3-chloro-3,4,4-trifluorobutanal (VII), without isolaton, with sodium chlorite/hydrogen peroxide to give 4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid (VIII) in overall unexpected yields;