Convenient Benzylic Bromination of 2-Hydroxy-5-methylisophthalaldehyde

Nikita Žoglo; Anton Mastitski; Vladislav Ivanistsev; Nadezda Kongi

doi:10.1021/acsomega.5c11342

Convenient Benzylic Bromination of 2-Hydroxy-5-methylisophthalaldehyde

Nikita Žoglo
, Anton Mastitski^*
, Vladislav Ivanistsev
, Nadezda Kongi^*

^*Šī darba korespondējošais autors

University of Tartu

Zinātniskās darbības rezultāts: Devums žurnālam › Zinātniskais raksts (žurnālā) › koleģiāli recenzēts

Kopsavilkums

A convenient and scalable method for the selective benzylic bromination of 2-hydroxy-5-methylisophthalaldehyde was developed, previously unreported in the literature. Direct Wohl–Ziegler conditions failed, suggesting the investigation of various protection strategies. A combination of methyl ether and geminal diacetate protecting groups gave rise to clean photochemical bromination with N-bromosuccinimide in PhCl, affording the benzyl bromide in 39% yield after recrystallization, which can be further functionalized or deprotected. This robust three-step procedure provides a practical pathway for the functionalization of isophthalaldehyde derivatives.

Oriģinālvaloda	Angļu
Lapas (no-līdz)	8442-8445
Žurnāls	ACS Omega
Sējums	11
Izdevuma numurs	5
DOIs	https://doi.org/10.1021/acsomega.5c11342
Publikācijas statuss	Publicēts - 10 febr. 2026

OECD Zinātnes nozare

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2.4 Ķīmijas inženierzinātne

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abstract = "A convenient and scalable method for the selective benzylic bromination of 2-hydroxy-5-methylisophthalaldehyde was developed, previously unreported in the literature. Direct Wohl–Ziegler conditions failed, suggesting the investigation of various protection strategies. A combination of methyl ether and geminal diacetate protecting groups gave rise to clean photochemical bromination with N-bromosuccinimide in PhCl, affording the benzyl bromide in 39\% yield after recrystallization, which can be further functionalized or deprotected. This robust three-step procedure provides a practical pathway for the functionalization of isophthalaldehyde derivatives.",

keywords = "Organic synthesis, Halogenation, Aromatic compounds, Alkyls",

author = "Nikita {\v Z}oglo and Anton Mastitski and Vladislav Ivanistsev and Nadezda Kongi",

note = "Publisher Copyright: {\textcopyright} 2026 The Authors. Published by American Chemical Society",

year = "2026",

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day = "10",

doi = "10.1021/acsomega.5c11342",

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AU - Žoglo, Nikita

AU - Mastitski, Anton

AU - Ivanistsev, Vladislav

AU - Kongi, Nadezda

PY - 2026/2/10

Y1 - 2026/2/10

N2 - A convenient and scalable method for the selective benzylic bromination of 2-hydroxy-5-methylisophthalaldehyde was developed, previously unreported in the literature. Direct Wohl–Ziegler conditions failed, suggesting the investigation of various protection strategies. A combination of methyl ether and geminal diacetate protecting groups gave rise to clean photochemical bromination with N-bromosuccinimide in PhCl, affording the benzyl bromide in 39% yield after recrystallization, which can be further functionalized or deprotected. This robust three-step procedure provides a practical pathway for the functionalization of isophthalaldehyde derivatives.

AB - A convenient and scalable method for the selective benzylic bromination of 2-hydroxy-5-methylisophthalaldehyde was developed, previously unreported in the literature. Direct Wohl–Ziegler conditions failed, suggesting the investigation of various protection strategies. A combination of methyl ether and geminal diacetate protecting groups gave rise to clean photochemical bromination with N-bromosuccinimide in PhCl, affording the benzyl bromide in 39% yield after recrystallization, which can be further functionalized or deprotected. This robust three-step procedure provides a practical pathway for the functionalization of isophthalaldehyde derivatives.

KW - Organic synthesis

KW - Halogenation

KW - Aromatic compounds

KW - Alkyls

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Convenient Benzylic Bromination of 2-Hydroxy-5-methylisophthalaldehyde

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