A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones Article Swipe
Yuki Yamamoto
,
Akihiro Tabuchi
,
Kazumi Hosono
,
Takanori Ochi
,
Kento Yamazaki
,
Shintaro Kodama
,
Akihiro Nomoto
,
Akiya Ogawa
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.3762/bjoc.17.198
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.3762/bjoc.17.198
A simple and efficient method for α-brominating lactones that affords α - bromolactones under mild conditions using tetraalkylammonium hydroxide (R 4 N + OH − ) as a base was developed. Lactones are ring-opened with Br 2 and a substoichiometric amount of PBr 3 , leading to good yields of the corresponding α-bromocarboxylic acids. Subsequent intramolecular cyclization over 1 h using a two-phase system (H 2 O/CHCl 3 ) containing R 4 N + OH − afforded α-bromo lactones in good yields. This method can be applied at the 10 mmol scale using simple operations. α-Bromo-δ-valerolactone, which is extremely reactive and difficult to isolate, could be isolated and stored in a freezer for about one week using the developed method. Optimizing the solvent for environmentally friendly large-scale syntheses revealed that methyl ethyl ketone (MEK) was as effective. In addition, in situ-generated α-bromo-δ-valerolactone was directly converted into a sulfur-substituted functional lactone without difficulty by reacting it with a sulfur nucleophile in one pot without isolation. This new bromination system is expected to facilitate the industrial use of α-bromolactones as important intermediates.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3762/bjoc.17.198
- https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-198.pdf
- OA Status
- diamond
- References
- 46
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4200261176
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4200261176Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3762/bjoc.17.198Digital Object Identifier
- Title
-
A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactonesWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
-
2021Year of publication
- Publication date
-
2021-12-09Full publication date if available
- Authors
-
Yuki Yamamoto, Akihiro Tabuchi, Kazumi Hosono, Takanori Ochi, Kento Yamazaki, Shintaro Kodama, Akihiro Nomoto, Akiya OgawaList of authors in order
- Landing page
-
https://doi.org/10.3762/bjoc.17.198Publisher landing page
- PDF URL
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https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-198.pdfDirect link to full text PDF
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YesWhether a free full text is available
- OA status
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diamondOpen access status per OpenAlex
- OA URL
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https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-198.pdfDirect OA link when available
- Concepts
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Chemistry, Halogenation, Nucleophile, Sulfur, Solvent, Hydroxide, Ketone, Intramolecular force, Organic chemistry, Ring (chemistry), Combinatorial chemistry, CatalysisTop concepts (fields/topics) attached by OpenAlex
- Cited by
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0Total citation count in OpenAlex
- References (count)
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46Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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