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^*

^*Corresponding author for this work

University of Tartu

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	8442-8445
Journal	ACS Omega
Volume	11
Issue number	5
DOIs	https://doi.org/10.1021/acsomega.5c11342
Publication status	Published - 10 Feb 2026

Keywords

Organic synthesis
Halogenation
Aromatic compounds
Alkyls

OECD Field of Science

1.4 Chemical Sciences
2.4 Chemical Engineering

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10.1021/acsomega.5c11342

Cite this

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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.",

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AU - Žoglo, Nikita

AU - Mastitski, Anton

AU - Ivanistsev, Vladislav

AU - Kongi, Nadezda

PY - 2026/2/10

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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

Abstract

Keywords

OECD Field of Science

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