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

Authors : Musa ERDOĞAN

Pages : 714-722

Doi:10.16984/saufenbilder.909041

View : 23 | Download : 8

Publication Date : 2021-06-30

Article Type : Research Paper

Abstract :In this paper, a new efficient method for the synthesis of 2-bromo-3-insert ignore into journalissuearticles values(bromomethyl);naphthalene is reported. The synthesis is based on insert ignore into journalissuearticles values(1); preparation of 1,4-dihydronaphthalene via Birch reduction with mild conditions from the reaction of naphthalene, and insert ignore into journalissuearticles values(2); the reaction between 1,4-dihydronaphthalene and dichlorocarbene generated in situ from chloroform and t-BuOK, and insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values(Br2);. This synthetic sequence allows simple preparation of 2-bromo-3-insert ignore into journalissuearticles values(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