Efficient Synthesis of Bis(dibromomethyl)arenes as Important Precursors of Synthetically Useful Dialdehydes

Agnieszka Bodzioch; Krzysztof Owsianik; Joanna Skalik; Emilia Kowalska; Anna Stasiak; Ewa Różycka-Sokołowska; Bernard Marciniak; Piotr Bałczewski

doi:10.1055/s-0035-1561651

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(20): 3509-3514
DOI: 10.1055/s-0035-1561651

paper

Efficient Synthesis of Bis(dibromomethyl)arenes as Important Precursors of Synthetically Useful Dialdehydes

Agnieszka Bodzioch*

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

,

Krzysztof Owsianik

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

,

Joanna Skalik

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

,

Emilia Kowalska

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

,

Anna Stasiak

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

,

Ewa Różycka-Sokołowska

^bJan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, 42-201 Częstochowa, Poland eMail: agabodz@interia.pl eMail: pbalczew@cbmm.lodz.pl

,

Bernard Marciniak

^bJan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, 42-201 Częstochowa, Poland eMail: agabodz@interia.pl eMail: pbalczew@cbmm.lodz.pl

,

Piotr Bałczewski*

^aDepartment of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland

^bJan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, 42-201 Częstochowa, Poland eMail: agabodz@interia.pl eMail: pbalczew@cbmm.lodz.pl

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Abstract

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Abstract

This work presents an efficient synthesis of bis(dibromomethyl)benzenes and a bis(dibromomethyl)thiophene as precursors of aromatic dialdehydes by bromination of dimethyl-substituted arenes under various reaction conditions (yields up to 99%). Several new variants of this reaction, including the use of N-bromosuccinimide (NBS) and bromine, and various solvents to replace carbon tetrachloride, benzene and carbon disulfide, were also tested. In the optimised protocols, the inconvenient solvents were replaced by 1,2-dichloroethane (DCE) and/or acetonitrile. In the DCE protocols, we reduced reaction times 24–32-fold, reduced the amount of NBS a fewfold and lowered power consumption relative to the literature protocols. The procedures also allowed elimination of long-lasting incandescent irradiation (100–500 W). The replacement of NBS by bromine led to a further reduction in the amount of brominating agent. The obtained bromo derivatives were efficiently converted into the corresponding dialdehydes (90–96%), which in turn are useful in materials chemistry.

Key words

bis(dibromination) - dialdehydes - radical reaction - solvents - bromine - N-bromosuccinimide

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