Preparation of 5-bromo-2-naphthol: The use of a sulfonic acid as a protecting and activating group

MolBank

Volumn 2009, Issue 3, 2009, Pages

  Everett, Renata ^a   Hamilton, Jillian ^a   Abelt, Christopher ^a  

^a Dept of Economics and Thomas Jefferson Program in Public Policy at the College of William and Mary   (United States)

Author keywords

Desulfonation; Protecting group; Sandmeyer reaction; Sulfonation

Indexed keywords

EID: 76749145917     PISSN: None     EISSN: 14228599     Source Type: Journal    
DOI: 10.3390/m602     Document Type: Article

References (12)

1. +-dependent deacetylase activity and SIR2-family members. PCT Int. Appl. WO 2007124383, 2007.
2. Pearlman, M. B. Phenols from certain carboxylic acids. US 2764587, 1956.
3. Dauben, W. G.; Saegebarth, K. A. Synthesis of β-(6-methoxy-1-naphthoyl)propionic acid. J. Am. Chem. Soc. 1951, 73, 1853-1854.
4. Bueno, A. B.; Flynn, C. J.; Gilmore, J.; Marcos, A.; Montero, C.; Porter, W.; Williams, A. C. A versatile protocol for the preparation of substituted1- and2-naphthyl piperazines from aminonaphthols. Tetrahedron Lett. 2005, 46, 7769-7771.
5. Ansink, H. R. W.; Zelvelder, E.; Cerfontain, H. Sulfonation of 1- and 2-Naphthol and their Methanesulfonate Esters with Sulfur Trioxide. The influence of initial sulfation on the sulfoproduct composition. Recl. Trav. Chim. Pay. B. 1993, 112, 210-215
6. Galli, C. Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical. Chem. Rev. 1988, 88, 765-792.
7. Wahl, H.; Basilios, H. Preparation of 2-naphthoic acid and 2-halonaphthalenes. Bull. Soc. Chim. Fr. 1947, 482-484.
8. Wolfe, W. C.; Doukas, H. M. 2-Bromonaphthalene. J. Chem. Ed. 1951, 28, 472-473.
9. Hanson, P.; Jones, J. R.; Taylor, A. B.; Walton, P. H.; Timms, A. W. Sandmeyer reactions. Part 7. An investigation into the reduction steps of Sandmeyer hydroxylation and chlorination reactions. J. Chem. Soc., Perkin Trans. 2 2002, 1135-1150.
10. Zollinger, H. In Diazo Chemistry I: Aromatic and Heteroaromatic Compounds; VCH, Weinheim, 1994; pp. 210-265.
11. Hanusek, J.; Macháček, V.; Lyčka, A. Reaction of 2-naphthol with substituted benzenediazonium salts in [bmim][BF4]. Dyes Pigments 2007, 73, 326-331, and ref. therein.
12. Fieser, L. F. 1,2-Aminonaphthol hydrochloride. Org. Synth. 1943, 2, 33-38.