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Paper | Regular issue | Vol 100, No. 9, 2020, pp.1405-1425
Published online, 6th July, 2020
DOI: 10.3987/COM-20-14292
■ Facile Preparation of 3,4-Benzocoumarins from 2-Arylbenzoic Acids with NCS and Nai

Momoko Nakamura and Hideo Togo*

*Graduate School of Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Treatment of 2-arylbenzoic acids with N-chlorosuccinimide (NCS) and NaI at 70 °C under fluorescent lighting condition gave the corresponding 3,4-benzocoumarins in good yields under transition-metal-free condition. It was found that the reactivity of NCS with NaI for the formation of 3,4-benzocoumarins from 2-arylbenzoic acids was as high as that with NIS. Thus, the formation of carboxyl radicals and their cyclization onto an aromatic ring from 2-arylbenzoic acids with much less expensive NCS and NaI, than NIS could be successfully carried out to form 3,4-benzocoumarins.