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

HRID 726116

Reaction equation

HRID 726116 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

6

Reactant 5

HCID 8023Ethyl vinyl etherHCID 96341,2-Dibromo-1-chloro-1,2,2-trifluoroethaneHCID 218364804-Bromo-3-chloro-3,4,4-trifluorobutanalHCID 86632281Sodium chlorite hydrogen peroxideHCID 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 isolation, with sodium chlorite/hydrogen peroxide to give 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) in overall unexpected yields;

Sources & evidence

ORD record
ord-da408afdec104d10ab586c6ceb20fbe1
Source dataset
uspto-grants-1998_01
Patent number
US05708032

Linked notes

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