NaBr/DMSO-Induced Synthesis of 2,5-Diformylfuran from Fructose or 5-(Hydroxymethyl)furfural

2,5‐Diformylfuran (DFF) was obtained by heating a solution of 5‐(hydroxymethyl)furfural in DMSO. The addition of acids or salts improved the selectivity, especially if bromides were employed. Good yields of DFF were obtained with HBr or NaBr as the catalyst. One‐pot procedures were developed from fr...

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Bibliographic Details
Published in:ChemCatChem 2014-05, Vol.6 (5), p.1195-1198
Main Authors: Laugel, Caroline, Estrine, Boris, Le Bras, Jean, Hoffmann, Norbert, Marinkovic, Sinisa, Muzart, Jacques
Format: Article
Language:English
Subjects:
2,5‐diformylfuran
5-diformylfuran
carbohydrates
Chemical Sciences
fructose
oxidation
oxygen heterocycles
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Summary:2,5‐Diformylfuran (DFF) was obtained by heating a solution of 5‐(hydroxymethyl)furfural in DMSO. The addition of acids or salts improved the selectivity, especially if bromides were employed. Good yields of DFF were obtained with HBr or NaBr as the catalyst. One‐pot procedures were developed from fructose, which led to DFF in medium yields. This transformation occurs through the formation of 5‐(bromomethyl)furan‐2‐carbaldehyde followed by a Kornblum‐type reaction. In the presence of bromide salts, the in situ formation of the catalyst involves the thermolysis of DMSO and the association of the resulting strong acids with the bromides. With a pinch of salt: The association of NaBr as a catalyst and DMSO as a solvent allows the synthesis of 2,5‐diformylfuran from 5‐(hydroxymethyl)furfural (HMF) or fructose in 75 or 50 % yield, respectively. This transformation occurs through the formation of 5‐(bromomethyl)furan‐2‐carbaldehyde followed by a Kornblum‐type reaction.
ISSN:1867-3880
1867-3899
1867-3899
DOI:10.1002/cctc.201400023