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Short Paper | Regular issue | Vol 96, No. 9, 2018, pp.1622-1630
Published online, 10th August, 2018
DOI: 10.3987/COM-18-13953
Cs2CO3-Promoted Vinylation of Phenols with Trichloroethylene: Facile Synthesis of (E)-1,2-Dichloro-1-phenoxyethenes

Kazunori Takahashi,* Naho Mamiya, Kei Fukushima, Masayoshi Tsubuki, and Toshio Honda

*Institute of Medicinal Chemistry, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan


An efficient method for the synthesis of (E)-1,2-dichloro-1-phenoxyethenes 2 has been developed. The reaction of phenol derivatives 1 with trichloroethylene at ambient temperature by means of Cs2CO3-DMSO system furnished the corresponding aryl vinyl ethers 2 in excellent yields. On the other hand, the same reaction of phenol derivatives 1i, 1k and 1p possessing an electron-withdrawing group at the o- or p-position of the hydroxy group required a harsh reaction conditions to heat at 70 °C for the synthesis of the desired products 2i, 2k and 2p.