An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene
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-dihydronaphthalen...
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Sakarya University
2021-06-01
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| Series: | Sakarya Üniversitesi Fen Bilimleri Enstitüsü Dergisi |
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| Online Access: | https://dergipark.org.tr/tr/download/article-file/1682160 |
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| author | Musa Erdoğan |
| author_facet | Musa Erdoğan |
| author_sort | Musa Erdoğan |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-a5087c4ab3c14edc8a2412226f25997a |
| institution | DOAJ |
| issn | 2147-835X |
| language | English |
| publishDate | 2021-06-01 |
| publisher | Sakarya University |
| record_format | Article |
| series | Sakarya Üniversitesi Fen Bilimleri Enstitüsü Dergisi |
| spelling | doaj-art-a5087c4ab3c14edc8a2412226f25997a2025-08-20T02:40:23ZengSakarya UniversitySakarya Üniversitesi Fen Bilimleri Enstitüsü Dergisi2147-835X2021-06-0125371472210.16984/saufenbilder.90904128An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthaleneMusa Erdoğan0https://orcid.org/0000-0001-6097-2862KAFKAS ÜNİVERSİTESİIn 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.https://dergipark.org.tr/tr/download/article-file/1682160metal-free synthesiseasy synthesisnaphthalenenaphthocyclopropane2-bromo-3-(bromomethyl)naphthalene |
| spellingShingle | Musa Erdoğan An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene Sakarya Üniversitesi Fen Bilimleri Enstitüsü Dergisi metal-free synthesis easy synthesis naphthalene naphthocyclopropane 2-bromo-3-(bromomethyl)naphthalene |
| title | An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene |
| title_full | An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene |
| title_fullStr | An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene |
| title_full_unstemmed | An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene |
| title_short | An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene |
| title_sort | efficient synthetic approach for the transition metal free preparation of 2 bromo 3 bromomethyl naphthalene from naphthalene |
| topic | metal-free synthesis easy synthesis naphthalene naphthocyclopropane 2-bromo-3-(bromomethyl)naphthalene |
| url | https://dergipark.org.tr/tr/download/article-file/1682160 |
| work_keys_str_mv | AT musaerdogan anefficientsyntheticapproachforthetransitionmetalfreepreparationof2bromo3bromomethylnaphthalenefromnaphthalene AT musaerdogan efficientsyntheticapproachforthetransitionmetalfreepreparationof2bromo3bromomethylnaphthalenefromnaphthalene |