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Synthesis 1999; 1999(2): 249-253
DOI: 10.1055/s-1999-3381
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A Practical Synthesis of Indanofan via One-Pot Bromination of 3-Chloroethylbenzene

Ken Tanaka* , Akemi Hosokawa, Kenji Yoshida
  • *Yokohama Research Center, Mitsubishi Chemical Corporation, 1000, Kamoshida-cho Aoba-ku, Yokohama, Kanagawa 227-8502, Japan; Fax 81(45)9 63 39 58; E-mail: Kenbo@atlas.rc.m-Kagaku.co.jp
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Publikationsdatum:
31. Dezember 1999 (online)

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A practical synthesis of Indanofan (1), a potent herbicide discovered by Mitsubishi Chemical Co. Ltd., was achieved starting from commercially available 3-chloroethylbenzene (2). 3-Chloro-α-bromostyrene (3), which was converted to 1-chloro-2-(3-chlorophenyl)prop-2-ene (5) in 2 steps, was synthesized via one-pot bromination of 2. 2-Ethylindane-1,3-dione (6) was synthesized from ethyl butyrate and ethyl phthalate (11) using NaOEt. The coupling reaction of 5 with 6 followed by oxidation with AcOOH afforded 1 in a high overall yield.

Indanofan - 3-chloro-α-bromostyrene - bromination - 3-chloroethylbenzene - 2-ethylindane-1,3-dione