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An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene      
Yazarlar
Doç. Dr. Musa ERDOĞAN Doç. Dr. Musa ERDOĞAN
Kafkas Üniversitesi, Türkiye
Özet
Herein, 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 formed in situ from chloroform and potassium tert-butoxide (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 tBuOK, followed by ring-opening of the cyclopropane via 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.
Anahtar Kelimeler
Makale Türü Özgün Makale
Makale Alt Türü Ulusal alan endekslerinde (TR Dizin, ULAKBİM) yayımlanan tam makale
Dergi Adı SAKARYA UNIVERSITY JOURNAL OF SCIENCE
Dergi ISSN 1301-4048
Dergi Tarandığı Indeksler TR DİZİN
Makale Dili İngilizce
Basım Tarihi 06-2021
Cilt No 25
Sayı 3
Sayfalar 714 / 722
Doi Numarası 10.16984/saufenbilder.909041
Makale Linki http://dx.doi.org/10.16984/saufenbilder.909041