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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.403-412
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)61
Synthesis of 4,4-Difluoro-α-tocopherol Using a Cross-coupling Reaction of Bromodifluoroacetate with Aryl Iodide in the Presence of Copper Powder

Kazuyuki Sato, Takashi Nishimoto, Kei Tamoto, Masaaki Omote, Akira Ando, and Itsumaro Kumadaki*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101, Japan

Abstract

Using our new methodology for introduction of a CF2 moiety, 4,4-difluoro-α-tocopherol (2) was synthesized. Thus, 1-iodo-2,5-bis(methoxy-methoxy)-3,4,6-trimethylbenzene (4) was treated with ethyl bromodifluoroacetate (1) in the presence of Cu powder to give a substituted phenyldifluoroacetate (5). Compound (5) was converted to 4,4-difluorochromanol derivative (12). Elongation of the side chain of 12 gave 2.