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Note | Regular issue | Vol 81, No. 1, 2010, pp.163-169
Published online, 27th October, 2009
DOI: 10.3987/COM-09-11837
New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide

Kazuhiro Kobayashi,* Taketoshi Kozuki, Shuhei Fukamachi, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


A new method to prepare 3,3-disubstituted phthalides [isobenzofuran- 1(3H)-ones] from α-substituted 2-bromostyrenes has been developed. The reaction of α-substituted 2-lithiostyrenes, generated in situ by bromine-lithium exchange between α-substituted 2-bromostyrenes and butyllithium, with carbon dioxide gave the corresponding lithium 2-vinylbenzoates, which upon treatment with concentrated hydrochloric acid afforded the desired products in one pot.