Synfacts 2007(12): 1258-1258  
DOI: 10.1055/s-2007-991361
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,3,6,7-Tetrabromonaphthalene Diimide

Contributor(s): Timothy M. Swager, Koushik Venkatesan
X. Gao, W. Qiu, X. Yang, Y. Liu*, Y. Wang, H. Zhang, T. Qi, Y. Liu, K. Lu, C. Du, Z. Shuai, G. Yu, D. Zhu*
Instiute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
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22. November 2007 (online)


The authors report the synthesis of 2,3,6,7-tetrabromonaphthalene diimide (TBNDI). Compound 2 was obtained in 96% yield by treatment of 1 with 5.3 equivalents of Br2 in a mixture of sulfuric acid and oleum at 140 °C for 4 weeks. Reaction of 2 with 4 equivalents of n-octylamines in refluxing acetic acid led to the formation of 3. Subsequent treatment with PBr3 in refluxing toluene for 12 hours afforded 4 in 41% yield.