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Synthesis 2011(2): 287-291  
DOI: 10.1055/s-0030-1258362
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Formylation of 2-(Dibromomethyl)-6,11-diphenyl-5,12-naphthacenequinone Using N,N-Dimethylformamide or N,N-Dimethylacetamide: Synthesis of 2-Formyl Rubrene

Yongfei Wanga, Hongbin Zhaoa, Zhizhi Hu*a, Masaru Kimura*a,b, Zhang Zhiqianga, Lei Penga, Koji Hiratsuka*c
a Optic Photo-electronic Materials and Research Development Center, University of Science and Technology Liaoning, Anshan 114044, P. R. of China
b Department of Chemistry, Faculty of Science, Okayama University, Tsushimanaka 3-1-1, Okayama 700-8530, Japan
c Chemistry Department, Faculty of Engineering, Gunma University, Tenjin-cho 1-5-1, Kiryu, Gunma 376-8515, Japan
Fax: +86(412)5612902; e-Mail: kimura-m@hotmail.com;
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Publication History

Received 5 August 2010
Publication Date:
14 December 2010 (online)

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Abstract

The main objective of this study is the synthesis of 2-formyl rubrene (5,6,11,12-tetraphenyltetracene-2-carbaldehyde). A smooth and efficient method for the formylation of 2-(dibromo­methyl)-6,11-diphenyltetracene-5,12-dione is described using N,N-dimethylformamide or N,N-dimethylacetamide as both the formylating agent and solvent, without any additional base. The product, 5,12-dioxo-6,11-diphenyl-5,12-dihydrotetracene-2-carbaldehyde is obtained in quantitative yield and is converted into the target compound via three additional steps.

Key words

2-formyl rubrene - aldehyde - formylation - N,N-dimethylformamide - N,N-dimethylacetamide