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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 13
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Original Articles

A New Route to 4-(2-Methoxyethyl) Phenol Via Palladium-Catalysed Arylation of Methyl Vinyl Ether

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Pages 1131-1136 | Published online: 19 Dec 2006

References

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  • Hallberg , A. and Westfelt , L. J. Chem. Soc. Perkin Trans. I , 1984 933
  • For selected methods for preparation of 3, see:
  • Lundmark , H. K. , Knott , D. M. , Sjöberg , K. and Åkermark , B. E. Belg. Pat. . 885,030 . 1980 . Chem. Abstr., 1981, 95, 115027t
  • Baron , M. , Chignac , M. , Grain , C. and Pigerol , C. Fr. Demande FR . 2,487,336 . 1982 . Chem. Abstr., 1982, 97, 5973g
  • Baron , M. , Chignac , M. , Grain , C. and Pigerol , C. Fr. Demande FR . 2,487,339 . 1982 . Chem. Abstr., 1982, 97, 5974h
  • Baron , M. , Chignac , M. , Grain , C. and Pigerol , C. Fr. Demande FR . 2,487,338 . 1982 . Chem. Abstr., 1982, 97, 23451q
  • Baron , M. , Chignac , M. , Grain , C. and Pigerol , C. Fr. Demande FR . 2,487,337 . 1982 . Chem. Abstr., 1982, 97, 23452r
  • Koch-Weser , J. 1979 . The New England Journal of Medicin , 301 : 698 and references therein.
  • Butyl vinyl ether was shown to behave identically with methyl vinyl ether, and was used for most of the experiments due to ease of handling.
  • Spencer , A. 1983 . J. Organomet. Chem. , 258 : 101 It has recently been reported that very high turnover numbers can be achieved for bromobenzene in Heck arylations, with sodium acetate as the base and triarylphosphine as ligand in dimethylformamide
  • Omitting the ligand improved the conversion and the regio-chemistry to some extent, but also gave extensive tar formation.
  • Jeffery , T. J. Chem. Soc. Chem. Commun. , 1984 1287 Normally, elevated temperatures are required for the arylation. A modification, utilizing phase transfer techniques, gave excellent yields when applied to iodobenzene, even at room temperature
  • Baird , R. and Winstein , S. 1963 . J. Am. Chem. Soc. , 85 : 567

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