An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Year 2021, Volume: 25 Issue: 3, 714 - 722, 30.06.2021

Musa Erdoğan

https://doi.org/10.16984/saufenbilder.909041

Abstract

In this paper, a new efficient method for the synthesis of 2-bromo-3-(bromomethyl)naphthalene is reported. The synthesis is based on (1) preparation of 1,4-dihydronaphthalene via Birch reduction with mild conditions from the reaction of naphthalene, and (2) the reaction between 1,4-dihydronaphthalene and dichlorocarbene generated in situ from chloroform and t-BuOK, and (3) access to the key intermediate 1H-cyclopropa[b]naphthalene from the reaction of 1,1-dichloro-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene with t-BuOK, followed by ring-opening of the three-membered cyclopropane by bromination with molecular bromine (Br2). This synthetic sequence allows simple preparation of 2-bromo-3-(bromomethyl)naphthalene in higher yields compared to the two previously reported syntheses. The synthetic approach is modular, low cost, and rapid, and can be utilized to synthesize building blocks of naphthalene derivatives.

Keywords

Metal-free synthesis, Easy synthesis, Naphthalene, Naphthocyclopropane, 2-Bromo-3-(bromomethyl)naphthalene

Thanks

The authors declare no conflict of interest. The author is greatly indebted to Prof. Dr. Arif DAŞTAN for providing use of all of his laboratory facilities throughout conducting the research.

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