An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene
Yazarlar (1)
Doç. Dr. Musa ERDOĞAN Kafkas Üniversitesi, Türkiye
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Özgün Makale
(Ulusal alan endekslerinde (TR Dizin, ULAKBİM) yayınlanan tam makale)
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| Dergi Adı | Sakarya University Journal of Science | ||
| Dergi ISSN | 1301-4048 Scopus Dergi | ||
| Dergi Tarandığı Indeksler | TR DİZİN | ||
| Makale Dili | İngilizce | Basım Tarihi | 06-2021 |
| Kabul Tarihi | 19-04-2021 | Yayınlanma Tarihi | 30-06-2021 |
| Cilt / Sayı / Sayfa | 25 / 3 / 714–722 | DOI | 10.16984/saufenbilder.909041 |
| Makale Linki | http://dx.doi.org/10.16984/saufenbilder.909041 | ||
| UAK Araştırma Alanları |
Organik Kimya
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| Özet |
| 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. |
| Anahtar Kelimeler |
| 2-Bromo-3-(bromomethyl)naphthalene | Easy synthesis | Metal-free synthesis | Naphthalene | Naphthocyclopropane |
BM Sürdürülebilir Kalkınma Amaçları
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