One-pot oxidative bromination – Esterification of aldehydes to 2-bromoesters using cerium (IV) ammonium nitrate and lithium bromide

[Display omitted] •Synthesis of α-bromoesters from aldehydes.•Solvent free mild conditions.•One-pot procedure. A two-step, one-pot reaction of aldehydes with the CAN/LiBr oxidation system under solvent-free conditions followed by the addition of methanol affords methyl α-bromocarboxylates. The oxida...

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Bibliographic Details
Published in:Tetrahedron letters 2017, Vol.58 (4), p.352-354
Main Authors: Nikishin, Gennady I., Kapustina, Nadezhda I., Sokova, Lyubov' L., Bityukov, Oleg V., Terent'ev, Alexander O.
Format: Article
Language:English
Subjects:
2-Bromoesters
Aldehydes
Bromination
Cerium (IV) ammonium nitrate (CAN)
Esterification
Oxidation
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Summary:[Display omitted] •Synthesis of α-bromoesters from aldehydes.•Solvent free mild conditions.•One-pot procedure. A two-step, one-pot reaction of aldehydes with the CAN/LiBr oxidation system under solvent-free conditions followed by the addition of methanol affords methyl α-bromocarboxylates. The oxidation of aldehydes with methanol using this system gives only methyl esters. A facile method, which does not require special equipment, was developed for the synthesis of 2-bromoesters from aliphatic aldehydes with carbon chain lengths of 5–10 atoms.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.12.036