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Paper | Regular issue | Vol 32, No. 9, 1991, pp.1805-1812
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5812
Selective Functionalization of 2,2’-Bithiophenes

Eugene Khor,* Siu Choon Ng, Hwee Chze Li, and Selenium Chai

*Department of Chemistry, National University of Singapore, 10 Kent Ridgh Crescent, 119260, Singapore

Abstract

The selective functionalization of the 2,2’-bithiophene molecule is described. Selective alkyl substitution at the 3,3’ positions was achieved by sequential bromination of the 3,3’ and 5,5’ positions followed by debromination at the 5,5’ positions. The resultant 3,3’-dibromo-2,2’-bithiophene was transformed via a Grignard reaction to give a series of 3,3’-dialkyl-2,2’-bithiophenes. Finally, nitration of the active 5,5’ positions gave the corresponding 3,3’-dialkyl-5,5’-dinitro-2,2’-bithiophenes.