An improved method for the synthesis of 3-fluorosalicylic acid with application to the synthesis of 3-(Trifluoromethyl)salicylic acid

Synthesis

Volumn , Issue 11, 1999, Pages 1878-1880

  Micklatcher, Mark L ^a   Cushman, Mark ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

3 (trifluoromethyl)salicylic acid; 3 fluorosalicylic acid; Bromine; Duff reaction; Electrophilic aromatic; Fluorine; Positional protective group

Indexed keywords

3 (TRIFLUOROMETHYL)SALICYLIC ACID; 3 FLUOROSALICYLIC ACID; PHENOL DERIVATIVE; SALICYLALDEHYDE; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEBROMINATION; DRUG SYNTHESIS; OXIDATION;

EID: 0032724717     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3607     Document Type: Article

References (10)

1. Cushman, M.; Casimiro-Garcia, A.; Hejchman, E.; Ruell, J. A.; Huang, M.; Schaeffer, C. A.; Williamson, K.; Rice, W. G.; Buckheit, R. W. Jr. J. Med. Chem, 1998, 41, 2076.
2. Cushman, M.; Golebiewski, W. M.; Graham, L.; Turpin, J.; Rice, W. G.; Fliakas-Woltz, V.; Buckheit, R. W. Jr. J. Med. Chem. 1996, 39, 3217.
3. Ferguson, L. N.; Reid, J. C.; Calvin, M. J. Am. Chem. Soc. 1946, 68, 2502.
4. Aldred, R.; Johnston, R.; Levin, D.; Nailan, J. J. Chem. Soc. Perkin Trans. 1 1994, 1823.
5. Ferguson, L. N.; Holmes, R, R.; Calvin, M. J. Am, Chem. Soc. 1950, 72, 5315.
6. Weidner-Wells, M. A.; Fraga-Spano, S. A. Syn. Comm. 1996, 26, 2775.
7. For a review, see: Tashiro, M. Synthesis 1979, 921.
8. Duff, J. C. J. Chem. Soc. 1941, 547.
9. Abubaker, A. B.; Booth, B. L.; Suliman, N. N. E.; Tipping, A. E. J. Fluorine Chem. 1992, 56, 359.
10. These ions are the result of direct El due to the volatility of the molecule.