N-Methylpyrrolidin-2-one hydrotribromide (MPHT) a mild reagent for selective bromination of carbonyl compounds: Synthesis of substituted 2-bromo-1-naphtols

Tetrahedron Letters

Volumn 46, Issue 24, 2005, Pages 4187-4191

  Bekaert, Alain ^a   Provot, Olivier ^a   Rasolojaona, Olimihamina ^a   Alami, Mouâd ^a   Brion, Jean Daniel ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

1 Tetralones; 2 Bromo 1 naphtols; Halogenation; MPHT

Indexed keywords

BROMINE DERIVATIVE; CARBONYL DERIVATIVE; N METHYLPYRROLIDIN 2 ONE HYDROTRIBROMIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 19044364172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.049     Document Type: Article

References (27)

1. R. Bolton D. Price B. Iddon B.J. Wakefield Bromine Compounds: Chemistry and Applications 1988 Elsevier Amsterdam 151
2. N. De Kimpe, and R. Verhé S. Patai Z. Rappoport The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines 1988 Wiley
3. For recent advances on α-bromination of carbonyl compounds, see: K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, and T. Horaguchi Chem. Commun. 2004 470 471
4. J.C. Lee, J.Y. Park, S.Y. Yoon, Y.H. Bae, and S.J. Lee Tetrahedron Lett. 45 2004 191 193
5. J.C. Lee, Y.H. Bae, and S.-K. Chang Bull. Korean Chem. Soc. 24 2003 407 408
6. H.Y. Choi, and D.Y. Chi Org. Lett. 5 2003 411 413
7. H.O. House, and W.C. McDaniel J. Org. Chem. 42 1977 2155 2160
8. C. Lambert, G. Nöll, E. Schmälzlin, K. Meerholz, and C. Bräuchle Chem. Eur. J. 4 1998 2129 2135
9. E. Hatzigrigoriou, S. Spyroudis, and A. Vargolis Liebigs Ann. Chem. 1989 167 170
10. H. Plieninger, and A. Völkl Chem. Ber. 109 1976 2121 2125
11. V.H. Tillu, P.D. Shinde, A.V. Bedekar, and R.D. Wakharkar Synth. Commun. 33 2003 1399 1403
12. M.J. Spitulnik Synthesis 1985 299 300
13. B. Sket, and M. Zupan Synth. Commun. 19 1989 2481 2487
14. J. Kosmrlj, M. Kocevar, and S. Polanc Synth. Commun. 26 1996 3583 3592
15. P. Satya, V. Gupta, R. Gupta, and A. Loupy Tetrahedron Lett. 44 2003 439 442
16. A. Bekaert, O. Barberan, M. Gervais, and J.-D. Brion Tetrahedron Lett. 41 2000 2903 2905
17. A. Bekaert, O. Barberan, E.B. Kaloun, A. Danan, J.-D. Brion, P. Lemoine, and B. Viossat Z. Kristallogr. NCS 216 2001 1 2
18. -1: 3339, 1640, 1420, 1228
19. W.E. Daniels, M.E. Chaddix, and S.A. Glickman J. Org. Chem. 28 1963 573 574
20. 4. Removal of the solvent yielded a crude product, which was purified by silica gel flash chromatography to afford 3 (see Table 1 for yields)
21. -1: 3441, 1585, 1497
22. M.A. Brimble, and T.J. Brenstrum J. Chem. Soc., Perkin Trans. 1 2001 1624 1631
23. Y.-Y. Jiang, Q. Li, W. Lu, and J.-C. Cai Tetrahedron Lett. 44 2003 2073 2075
24. 3CN (10 mL) was stirred in an oil bath at 80°C for 18 h. The reaction mixture was cooled and treated as above (Ref. 13)
25. E. Mosettig, and L.M. Everette J. Org. Chem. 5 1940 528 536
26. W.K. Brewster, D.E. Nichols, V.J. Watts, R.M. Riggs, D. Mottola, and R.B. Mailman J. Med. Chem. 38 1995 318 327
27. A.H. Hulme, S.S. Henry, and A.I. Meyers J. Org. Chem. 60 1995 1265 1270