Arylmethanesulfonates are convenient latent phenols in the nucleophilic aromatic substitution reaction

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 3989-3990

  Dinsmore, Christopher J ^a   Zartman, C Blair ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALOGENIDE; ARYLMETHANESULFONIC ACID DERIVATIVE; DIARYLETHER; ETHER DERIVATIVE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033591152     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00660-7     Document Type: Article

References (13)

1. 1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991, p. 169.
2. 2. (a) Looker, J. H.; Thatcher, D. N. J. Org. Chem. 1954, 19, 784.
3. (b) MaloneyHuss, K. E.; Portoghese, P. S. J. Org. Chem. 1990, 55, 2957.
4. (c) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C; Katz, J. L. Angew. Chem. Int. Ed. 1998, 37, 2700.
5. (d) Baldwin, J. E.; Barton, D. H. R.; Dainis, I.; Pereira, J. L. C. J. Chem. Soc. C 1968, 2283.
6. 3. (a) Paradisi, C. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p. 423.
7. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, III, W. J. J. Org. Chem. 1998, 63, 6338, and references cited therein.
8. 4, reflux. (c) 2-pyrrolidinone, NaH, DMF, 0 °C.
9. 2) yielded 385 mg of diarylether 3a as a yellow solid (97% yield).
10. 1H NMR and HRMS spectral data consistent with the assigned structures.
11. 3) should not be excluded.
12. 3, DMSO, 80 °C) HPLC analysis indicated complete conversion of 1d to 4-nitropnenol within 10 minutes, then gradual conversion to diarylether 3d over 7 hours. Compound 1c gave diarylether 3c at a slower rate without detectable accumulation of 4-methoxyphenol.
13. 1H NMR analysis to confirm ≥95% diastereomer purity.