OOxidative bromination of activated aromatic compounds using aqueous nitric acid as an oxidant

Organic Process Research and Development

Volumn 8, Issue 4, 2004, Pages 568-570

  Joshi, Ashutosh V ^a   Baidossi, Mubeen ^a   Mukhopadhyay, Sudip ^b   Sasson, Yoel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BROMINE DERIVATIVE; NITRIC ACID; OXIDIZING AGENT;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; CHLORINATION; OXIDATION;

EID: 4243059492     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op030055w     Document Type: Article

References (31)

1. (a) Ullmann's Encyclopedia of Industrial Chemistry, 6th ed.; Wiley-VCH: 2002.
2. (b) Davis, S. G. Organotransition Metal Chemistry: Application to organic synthesis; Pergamon Press: Oxford, 1982.
3. Sasson, Y. In The chemistry of functional group Suppl. D2: The Chemistry of halides, pseudo-halides and azides Part 1; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: 1995.
4. Bray, W. C.; Livinston, R. S. J. Am. Chem. Soc. 1928, 50, 1654.
5. Mukhopadhyay, S.; Ananthakrishnan, S.; Chandalia, S. B. Org. Process Res. Dev. 1999, 3, 451.
6. (a) Bhattacharjee, M. Polyhedron 1992, 11, 2817.
7. (b) Rothenberg, G.; Clark, J. H.; Green Chem. 2000, 2, 248.
8. (c) Bora, U.; Bose, G.; Chaudhari, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Org. Lett. 2000, 2, 247.
9. (d) Conte, V.; Di Furia, F.; Moro, S. Tetrahedron Lett. 1994, 35, 7249.
10. (e) Conte, V.; Di Furia, F.; Moro, S. Tetrahedron Lett. 1996, 37, 8609.
11. (f) Neumann, R.; Assael, I. J. Chem. Soc., Chem. Commun. 1988, 1285.
12. (a) Narender, N.; Srinivasu, P.; Prasad, M. R.; Kulkarni, S. J.; Raghavan, K. V. Synth. Commun. 2002, 32, 2313.
13. (b) Groweiss, A. Org. Process Res. Dev. 2000, 4, 30.
14. (c) Hirano, M.; Monobe, H.; Yakabe, S.; Morimoto, T. Synth. Commun. 1998, 28, 1463.
15. (a) Dakka, J.; Sasson, Y. J. Chem. Soc., Chem. Commun. 1987, 1421.
16. (b) Mukhopadhyay, S.; Mukhopadhyaya, J. K.; Ponde, D. E.; Cohen, S.; Kurkalli, B. Org. Process Res. Dev. 2000, 4, 509.
17. (c) Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55, 11127.
18. (d) Vyas, P. J.; Bhatt, A. K.; Ramchandraiah, G.; Bedekar, A. V. Tetrahedron Lett. 2003, 44, 4085.
19. (e) Deshmukh, A. P.; Padiya, K. J.; Jadhav, V. K.; Salunkhe, M. M. J. Chem. Res., Synop. 1998, 828.
20. (a) Neidleman, S. L.; Geigert, J. Biohalogenation; Ellis Horwood: Chichester, 1986.
21. (b) Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937.
22. (c) Martinez-Perez, J. A.; Pickel, M. A.; Caroff, E.; Woggon, W.-D. Synlett 1999, 1875.
23. Rothenberg, G.; Clark, J. H. Org. Process Res. Dev. 2000, 4, 270 and see ref 6 therein.
24. Joshi, A. V.; Baidoosi, M.; Mukhopadhyay, S.; Sasson. Y. Org. Process Res. Dev. 2003, 7, 95.
25. Cheprakov A. V.; Makhonkov, D. I.; Rodkin, M. A.; Beletskaya, I. P. Zh. Org. Khim. 1988, 24, 248.
26. (a) Iqbal, S.; Anwar, M.; Munawar, M. A.; Siddiq, M. J. Chem. Soc. Pak. 1992, 14, 212.
27. (b) Marterer, W.; Prikoszovich, W.; Wiss, J.; Prashad, M. Org. Process Res. Dev. 2003, 7, 318 and references therein.
28. (a) Hashem, A. I. J. Appl. Chem. Biotechnol. 1972, 22, 1223.
29. (b) Datta, R. L.; Chatterjee, N. R. J. Am. Chem. Soc. 1916, 38, 2545.
30. Currie, F.; Holmberg, K.; Westman, G. Colloid Surf., A 2003, 215, 51.
31. Vogel A. I. A Text-Book of Quantitative inorganic Analysis including Elementary Instrumental Analysis, 3rd ed.; Longmans: 1961.