A practical synthesis of highly hindered biphenyl-2-carboxylates via nucleophilic aromatic substitution of tert-butyl 2-methoxybenzoates with aryl grignard reagent

Organic Process Research and Development

Volumn 5, Issue 5, 2001, Pages 535-538

  Aki, Shinji ^a   Haraguchi, Yoshikazu ^a   Sakikawa, Hiroshi ^a   Ishigami, Masashi ^a   Fujioka, Takafumi ^a   Furuta, Takuya ^a   Minamikawa, Jun Ichi ^a  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035537548     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0001279     Document Type: Article

References (33)

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10. The synthetic procedure was reported, see: (a) Aki, S.; Haraguchi, Y.; Tone, H.; Fujioka, T.; Ishigami, M.; Sakikawa, H.; Minamikawa, J.; Nishi, T.; Tanaka, T.; Watanabe, K. Jpn. Kokai Tokkyo Koho JP11-217348, 1999; Chem. Abstr. 1999, 131, 129765f. (b) Scammells, P. J.; Baker, S. P.; Beauglehole, A. R. Bioorg. Med. Chem. 1998, 6, 1517. (c) Hong, F.-T.; Lee, K.-S.; Tsai, Y.-F.; Liao, C.-C. J. Chin. Chem. Soc. (Taipei) 1998, 45, 1.
11. The synthetic procedure was reported, see: (a) Aki, S.; Haraguchi, Y.; Tone, H.; Fujioka, T.; Ishigami, M.; Sakikawa, H.; Minamikawa, J.; Nishi, T.; Tanaka, T.; Watanabe, K. Jpn. Kokai Tokkyo Koho JP11-217348, 1999; Chem. Abstr. 1999, 131, 129765f. (b) Scammells, P. J.; Baker, S. P.; Beauglehole, A. R. Bioorg. Med. Chem. 1998, 6, 1517. (c) Hong, F.-T.; Lee, K.-S.; Tsai, Y.-F.; Liao, C.-C. J. Chin. Chem. Soc. (Taipei) 1998, 45, 1.
12. The synthetic procedure was reported, see: (a) Aki, S.; Haraguchi, Y.; Tone, H.; Fujioka, T.; Ishigami, M.; Sakikawa, H.; Minamikawa, J.; Nishi, T.; Tanaka, T.; Watanabe, K. Jpn. Kokai Tokkyo Koho JP11-217348, 1999; Chem. Abstr. 1999, 131, 129765f. (b) Scammells, P. J.; Baker, S. P.; Beauglehole, A. R. Bioorg. Med. Chem. 1998, 6, 1517. (c) Hong, F.-T.; Lee, K.-S.; Tsai, Y.-F.; Liao, C.-C. J. Chin. Chem. Soc. (Taipei) 1998, 45, 1.
13. The synthetic procedure was reported, see: (a) Aki, S.; Haraguchi, Y.; Tone, H.; Fujioka, T.; Ishigami, M.; Sakikawa, H.; Minamikawa, J.; Nishi, T.; Tanaka, T.; Watanabe, K. Jpn. Kokai Tokkyo Koho JP11-217348, 1999; Chem. Abstr. 1999, 131, 129765f. (b) Scammells, P. J.; Baker, S. P.; Beauglehole, A. R. Bioorg. Med. Chem. 1998, 6, 1517. (c) Hong, F.-T.; Lee, K.-S.; Tsai, Y.-F.; Liao, C.-C. J. Chin. Chem. Soc. (Taipei) 1998, 45, 1.
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20. Due to the toxicity, we the authors did not examine the reaction in HMPA.
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23. NAr reaction of N-alkyl-substituted benzaldimine with aryl Grignard reagents was reported, see: (a) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732.
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26. The following result was reported: treating i-propyl 2-methoxybenzoate with phenylmagnesium bromide gave diphenyl(2-methoxyphenyl)methanol in 75% yield; see: ref 6a.
27. A similar type of reaction was reported, see: Fuson, R. C.; Speck, S. B. J. Am. Chem. Soc. 1942, 64, 2446.
28. The required tert-butyl ester 3d was readily prepared by esterification of the corresponding carboxylic acid with thionyl chloride followed by treatment with tert-butyl alcohol and potassium carbonate in dichloromethane in 91% yield. For preparation of 3e, the transesterification technique was more effective, see: (a) Rossi, R. A.; de Rossi, R. H. J. Org. Chem. 1974, 39, 855.
29. (b) Stanton, M. G.; Gagne, M. R. J. Org. Chem. 1997, 62, 8240.
30. The use of THF-toluene as a cosolvent gave better results; the reaction of 3d with 4a (3 equiv) in THF gave 82% of 5d after refluxing for 15 h.
31. 4, 482.3398; found 482.3367.
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33. + 464.