A Practical Preparation of Methyl 4-(Trimethylsilyl)-benzoate: An Intermediate in the Synthesis of SDZ 63135

References

• Houlihan , William and Cheon , Seung H. United States Pat. 4992428A . 1991 .
   Google Scholar
• Houlihan , William . United States Pat. 4910206A . 1990 .
   Google Scholar
• Houlihan , William . World Pat. 8800587 . 1988 .
   Google Scholar
• Danhauser-Riedl Susanne . 1991 . Cancer Res. , 51 ( 1 ) : 43
   PubMed Web of Science ®Google Scholar
• Yamamoto , K. , Hayashi , A. , Suzuki , S. and Tsuji , Jiro . 1987 . Organometallics , 6 : 974 For literature preparations of methyl (4-trimethylsilyl) benzoate 1, see:
   Web of Science ®Google Scholar
• Picard , J. P. 1979 . J. Org. Chem. , 44 ( 3 ) : 420
   Web of Science ®Google Scholar
• Eaborn , C. and Jackson , P. M. 1969 . J. Chem. Soc B , 21
   Google Scholar
• The generation of MnO2 created waste disposal problems
   Google Scholar
• Reimann , E. and Langwieler , I. 1975 . Archiv. Pharm. , 11 ( 308 ) : 888 For literature preparations of (4-bromophenyl) trimethylsilane 4, see:
   Google Scholar
• Moerlein , S. M. 1987 . J. Organomet. Chem. , 319 : 29
   Google Scholar
• Glyde , E. and Taylor , R. 1973 . J. Chem. Soc. Perkin Trans. , I : 1632
   Google Scholar
• Effenberger , F. and Haebich , D. 1979 . Liebigs Ann. Chem , 842
   Google Scholar
• Schraml , J. , Chvalovsky , V. , Maegi , M. and Lippmaa , E. 1975 . Coll. Czech. Chem. Comm. , 140 : 897
   Google Scholar
• Gilman , H. , Melvin , H. W. and Goodman , J. J. 1954 . J. Am. Chem. Soc. , 76 : 3219
   Google Scholar
• Chvalovsky , V. and Bazant , V. 1951 . Coll. Czech. Chem. Comm. , 16 : 580
   Google Scholar
• Jones , R. G. and Gilman , H. 1951 . Org. Reactions , 6 : 339
   Google Scholar
• Roberts , J. D. , McElhill , E. A. and Armstrong , R. 1949 . J. Am. Chem. Soc. , 71 : 2923
   Google Scholar
• Burkhard , C. A. 1946 . J. Am. Chem. Soc. , 68 : 2103
   Google Scholar
• Stephens , E. B. , Kinsey , K. E. , Davis , J. F. and Tour , J. M. 1993 . Macromolecules , 26 : 3519 For lithium-bromine exchange reactions with 1, 4-dibromobenzene, see:
   Google Scholar
• Tour , J. M. and Stephens , E. B. 1991 . Poly. Mater. Sci. Eng. , 64 : 223
   Google Scholar
• Tour , J. M. and Stephens , E. B. 1991 . J. Am. Chem. Soc. , 113 : 2309
   Google Scholar
• Brandsma , L. and Verkruijsse , H. D. 1987 . “Preparative Polar Organometallic Chemistry” , volume 1 , 190 Berlin : Springer-Verlag .
   Google Scholar
• Diethyl ether is not acceptable for large scale preparations due to its extremely low flashpoint
   Google Scholar
• t-Butyllithium is pyrophoric and prohibited for use in our pilot plant operations
   Google Scholar
• Whitmore , F. C. and Loder , D. J. Org. Synth., Coll. , Vol. II 282 For methoxycarbonylation of an aryl magnesium bromide, see:
   Google Scholar
• Bromosilane 4 can be purified by short path distillation: 105–115 °C, 25–30 mm Hg (Lit.: 74–76°C, 2.5 mm, see ref. 5h).
   Google Scholar
• Reverse addition gave a lower yield (39%).
   Google Scholar
• Houlihan , W. J. and Parrino , V. A. 1982 . J. Org. Chem. , 47 ( 26 ) : 5177 For the preparation of 7, see:
   Web of Science ®Google Scholar
• Piskov , V. B. , Kasperovich , V. P. and Yakovleva , L. M. 1976 . Khim. Geterotsikl. Soedin. , 8 : 1112
   Google Scholar