4,5-Difluorophthalic Anhydride → 3,4-Difluorobenzoic acid

HRID 2108226Notes

Reaction equation

HRID 2108226 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8]C(=O)[C:5]2=[CH:11][C:12]=1[F:13].FC1C=C(C(O)=O)C(=CC=1F)C(O)=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:11][C:12]=1[F:13])[C:9]([OH:10])=[O:8]

Participants

3

Reactant 2

HCID 6397454,5-Difluorophthalic AnhydrideHCID 6433824,5-Difluorophthalic Acid

Product 1

HCID 991663,4-Difluorobenzoic acid

Procedure

4,5-Difluorphthalic anhydride and 4,5-difluorophthalic acid may be decarboxylated in high yield to 3,4-difluorobenzoic acid by heating in N-methyl-2-pyrrolidone or dimethyl acetamide using copper, copper oxide, copper salts, or halides and salts of Zn, Cd, Ag and Ni as a catalyst.

Sources & evidence

ORD record
ord-ba4ad89726594038aca240611429452f
Source dataset
uspto-grants-1990_06
Patent number
US04937377

Reaction notes

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