Simple and regioselective bromination of 5,6-disubstituted-indan-1-ones with Br2 under acidic and basic conditions

Molecules

Volumn 12, Issue 1, 2007, Pages 74-85

  Choi, Taeyoung ^a   Ma, Eunsook ^a  

^a Catholic University of Daegu   (South Korea)

Author keywords

bromination; 5,6 dihydroxyindan 1 one; 5,6 Dimethoxyindan 1 one; Regioselective aromatic bromination

Indexed keywords

ACETIC ACID; BROMINATED HYDROCARBON; BROMINE; HYDROXIDE; INDAN DERIVATIVE; POTASSIUM DERIVATIVE; POTASSIUM HYDROXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; TEMPERATURE;

ACETIC ACID; BROMINE; HYDROCARBONS, BROMINATED; HYDROGEN-ION CONCENTRATION; HYDROXIDES; INDANS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; POTASSIUM COMPOUNDS; TEMPERATURE;

EID: 33846966660     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12010074     Document Type: Article

References (27)

1. Taylor, R. (Ed.); Electrophilic aromatic substitution; John Wiley & Sons: Chichester, 1990.
2. Diederich, F., Stang, P. J. Metal-catalyzed cross-coupling reactions; Wiley-VCH: Weinheim, Germany, 1998.
3. Jacquesy, J.; Jouannetaud, M.; Makani, S. meta-Bromination of phenols in superacids. J. Chem. Soc. Commun. 1980, 110-111.
4. Duan, J.; Zhang, L. H.; Dolbier, W. R., Jr. A convenient new methods for the bromination of deactivated aromatic compounds. Synlett. 1999, 1245-1246.
5. Auerbach, J. Weissman, S. A.; Blacklock, T. J. N-Bromosuccinimide/ dibromodimethylhydantoin in aqueous base: A practical method for the bromination of activated benzoic acids. Tetrahedron Lett. 1993, 34, 931-934
6. Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Halogenation of aromatic compounds by N-chloro, N-bromo, and N-iodosuccinimide. Chem. Lett. 2003, 32, 932-933.
7. Barhate, N. B.; Gajare A. S.; Wakharkar, R. D.; Bedekar, A. V. Simple and efficient chlorination and bromination of aromatic compounds using aqueous TBHP (or H2O2) and a hydrohalic acid. Tetrahedron Lett. 1998, 39, 6349-6350.
8. Majetich, G.; Hicks, R.; Reister, S. Electrophilic aromatic bromination using bromodimethyl-sulfonium bromide generated in situ. J. Org. Chem. 1997, 62, 4321-4326.
9. 3COOH. Synth. Commun. 2004, 34, 2143-2152.
10. 2 over microporous catalysts. Tetrahedron Lett. 2005, 46, 4465-4468.
11. Chiappe, C.; Leandri, E.; Pieraccini, D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent. Chem. Commun. 2004, 2536-2537.
12. Narender, N.; Sriniva, P.; Ramakrishna, M.; Kilkarmi, S. J. Reghaven K. V. An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and Oxone®. Synth. Commun. 2002, 32, 2313-2318.
13. Doyle, M. P.; Van Lente, M. A.; Mowat, R.; Fobare, W. F. Alkyl nitrite-metal halide deamination reactions. 7. Synthetic coupling of elctrophilic bromination with substitutive deamination 7J. Org. Chem. 1980, 45, 2570-2575.
14. Park, M. Y.; Yang, S. G.; Jadhav, V.; Kim, Y. H. Practical and regioselective brominations of aromatic compounds using tetrabutylammonium peroxydisulfate. Tetrahedron Lett. 2004, 45, 4887-4890.
15. Ozgun, B.; Degirmenbasi, N. Quinolium bromochromate - A new reagent for bromination and oxidation. Synth. Commun. 1996, 26, 3601-3601.
16. Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. A mild and efficient procedure for alpha-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate. Chem. commun. 2004, 470-471.
17. Lee, J. C.; Park, J. Y.; Yoon, S. Y.; Bae, Y. H.; Bae, Y. H.; Lee, S. J. Efficient microwave induced direct α-bromination of carbonyl compounds. Tetrahedron Lett. 2004, 45, 191-193
18. Lee, J. C.; Bae, Y. H.; Chang, S.-K. Efficient a-halogenation of carbonyl compounds by N-bromosuccinimide and N-chlorosuccinimides. Bull. Korea Chem. Soc. 2003, 24, 407-408.
19. Bertelsen, S.; Halland, N.; Bachmann, S.; Marigo, M.; Braunton, A.; Jorgensen, K. A. Organocatalytic asymmetric α-bromination of aldehydes and ketones. Chem Commun. 2005, 4821-4823.
20. Choi, H. Y.; Chi, D. Y. Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon. Org. Lett. 2003, 5, 411-414.
21. Bekaert, A.; Provot, O.; Rasolojaona, O.; Alami, M.; Brion, J.-D. N-Methylpyrrolidin-2-one hydrobromide (MPHT) a mild reagent for selective bromination of carbonyl compounds : Synthesis of substituted 2-bromo-1-naphthols. Tetrahedron Lett. 2005, 46, 4187-4191.
22. Jung, W.; Ma, E. Synthesis of 2-(5,6-dimethoxy-1-indenyl)ethylamine. Yakhak Hoeji 2003, 47, 1-4.
23. Sonesson, C. ; Barf, T. ; Nilsson, J. ; Dijkstra, D. ; Carlsson, A. ; Svensson, K. ; Smith, M. W. ; Martin, I. J.; Duncan, J. N.; King, L. J.; Wikstrom, H. Synthesis and evaluation of pharmacological and pharmacokinetic properties of monopropyl analogs of 5-, 7-, and 8-[[(trifluoromethyl)-sulfonyl] oxy]-2-aminotetralines: Central dopamine and serotonin receptor activity. J. Med. Chem. 1995, 38, 1319-1329.
24. Ma, E. Synthesis of 2-amino-5,6-difluoroindanI·HCl. Yakhak Hoeji 1999, 43, 751-755.
25. Logan, R. T.; Redpath, J.; Roy, R. G. Indene and naphthalene derivatives. US Pat. 4705782, 1987.
26. Johnson, W. S.; Shelberg, W. E. A plan for distinguishing between some five- and six-membered ring ketones. J. Am. Chem. Soc. 1945, 67, 1745-1754.
27. House, H. O.; McDaniel, W. C. Perhydroindan derivatives. 18. The use of indenone ketals as dienophiles. J. Org. Chem. 1977, 42, 2155-2163.