A synthesis of selected o,o′-disubstituted diarylacetic esters and diarylmethanes

Organic Preparations and Procedures International

Volumn 37, Issue 6, 2005, Pages 550-555

  Bunce, Richard A ^a   Schammerhorn, James E ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIARYLMETHANES;

EID: 30044443466     PISSN: 00304948     EISSN: None     Source Type: Journal    
DOI: 10.1080/00304940509354984     Document Type: Article

References (13)

1. R. A. Bunce and J. E. Schammerhorn, J. Heterocycl. Chem., Submitted.
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3. D. J. Bull, M. J. Fray, M. C. Mackenny and K. A. Malloy, Synlett, 647 (1996).
4. R. A. Bunce, M. H. Randall and K. G. Applegate, Org. Prep. Proced. Int., 34, 493 (2002).
5. (a) R. L. Augustine, A. J. Gustavsen, S. F. Wanat, I. C. Pattison, K. S. Houghton and G. Koletar, J. Org. Chem., 38, 3004 (1973).
6. (b) M. Perchinunno, A. Guerrato and F. Pregnolato, Org. Prep. Proced. Int., 9, 303 (1977).
7. This diester was prepared by dissolving homophthalic acid in methanol containing a catalytic amount of concentrated sulfuric acid and refluxing overnight with removal of water using 3Å molecular sieves according to the procedure given in H. R. Harrison, W. M. Haynes, P. Arthur and E. J. Eisenbraun, Chem. Ind. (London), 1568 (1968).
8. R. A. Bunce and L. B. Johnson, Org. Prep. Proced. Int., 31, 407 (1999).
9. (2-Benzoylphenyl)acetic acid was prepared according to T. de Paulis, C. R. Ross Betts, H. E. Smith, P. L. Mobley, D. H. Manier and F. Sulser, J. Med. Chem., 24, 1021 (1981) and esterified using the general method given in ref 6.
10. R. A. Bunce, D. M. Herron, L. B. Johnson and S. V. Kotturi, J. Org. Chem., 66, 2822 (2001).
11. An attempt was also made to generate products resulting from nucleophilic aromatic substitution of 1a and 1b with 4-fluoro-1-nitrobenzene. While the initial addition was successful in each case, the yields were 10-25% lower than reactions with 2-fluoro-1-nitrobenzene. Additionally, the hydrolysis- decarboxylation procedure gave products that were more difficult to purify. Thus, we did not investigate additional substitution patterns.
12. J. E. McMurry, Org. React., 24, 187 (1976).
13. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).