[emim]BF4-promoted chloromethylation of aromatic hydrocarbons

Synthetic Communications

Volumn 36, Issue 20, 2006, Pages 3053-3059

  Wang, Yun ^a   Shang, Zhi Cai ^a   Wu, Tian Xing ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Aromatic hydrocarbons; Chloromethylation; Ionic liquid emim BF4

Indexed keywords

1 ETHYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; AROMATIC HYDROCARBON; BORON TRIFLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHLOROMETHYLATION; METHYLATION; PRODUCT RECOVERY; REACTION ANALYSIS;

EID: 33750081736     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600775267     Document Type: Article

References (25)

1. Fuson, R. C.; McKeever, C. H. Organic Reactions; John Wiley: New York, 1943; Vol. 1, pp. 63-90.
2. Olah, G. A. Friedel Crafts and Related Reactions; John Wiley: New York, 1964; Vol. 2, Part 2, pp. 659-784.
3. Wood, J. H.; Perry, M. A.; Tung, C. C. The bis-chloromethylation of aromatic compounds. J. Am. Chem. Soc. 1950, 2989.
4. Wood, J. H.; Perry, M. A.; Tung, C. C. The Sommelet reaction in the synthesis of aromatic dialdehydes. J. Am. Chem. Soc. 1950, 72, 2992.
5. Shacklett, C. D.; Smith, H. A. The application of the chromethylation reaction to the syntheses of certain polymethylbenzenes. J. Am. Chem. Soc. 1951, 73, 766.
6. Sasaki, T.; Hasebe, Y.; Okada, S.; Arai, T. 1988, Jpn. Kokai Tokkyo Koho JP63-048234.
7. Gerisch, M.; Krumper, J. R.; Bergman, R. G.; Don Tilley, T. Rhodium(III) and rhodium(II) complexes of novel bis(oxazoline) pincer ligands. Organometallics 2003, 22, 47.
8. Anastas, P. T., Williamson, T. C., Eds. Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes; Oxford University Press: Oxford, 1998.
9. Kishida, T.; Yamauchi, T.; Kubota, Y.; Sugi, Y. Rare-earth metal triflates as versatile catalysts for the chloromethylation of aromatic hydrocarbons. Green Chem. 2004, 6, 57.
10. Nishida, T.; Tashiro, Y.; Yamamoto, M. Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte. J. Fluorine Chem. 2003, 120, 135.
11. Wilkes, J. S.; Levisky, J.; Wilson, R. A.; Hussey, C. L. Dialkylimidazolium chloroaluminate melts: A new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis. Inorg. Chem. 1982, 21, 1263.
12. (a) Sheldon, R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399;
13. (b) Admas, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R. Friedel-Crafts reactions in room temperature ionic liquids. Chem. Commun. 1998, 2097;
14. (c) Gordon, C. M.; McCluskey, A. Ionic liquids: A convenient solvent for environmentally friendly allylation reactions with tetraallystannane. Chem. Commun. 1999, 1431;
15. (d) Admas, C.; Earle, M. J.; Seddon, K. R. Catalytic cracking reactions of polyethylene to light alkanes in ionic liquids. Green Chem. 2000, 2, 21.
16. Huddleston, J. G.; Williams, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room temperature ionic liquids as novel media for "clean" liquid-liquid extraction. Chem. Commun. 1998, 1765.
17. (a) Yeung, K. S.; Farkas, M. E.; Qiu, Z. L.; Yang, Z. Friedel-Crafts acylation of indoles in acidic imidazolium chloroaluminate ionic liquid at room temperature. Tetrahedron Lett. 2002, 43, 5793;
18. (b) Nara, S. J.; Harjani, J. R.; Salunkhe, M. M. Friedel-Crafts sulfonylation in 1-butyl-3-methylimidazolium chloroaluminate ionic liquids. J. Org. Chem. 2001, 66, 8616.
19. (a) Jorapur, Y. R.; Lee, C. H.; Chi, D. Y. Mono- and dialkylations of Pyrrole at C2 and C5 positions by nucleophilic substitution reaction ionic liquid. Org. Lett. 2005, 7, 1231;
20. 6. Tetrahedron Lett. 2003, 44, 981;
21. (c) Corey, E. J.; Bo, Y.; Busch-Peterson, J. Highly Enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent: Application and mechanism. J. Am. Chem. Soc. 1998, 120, 13000.
22. (a) Suarez, P. A. Z.; Dulliu, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes. Polyhedron 1996, 15, 1217;
23. (b) Bonhote, P.; Dias, A.-P.; Papageorigu, N.; Kalyanasundaram, K.; Gratzel, M. Hydrophobic, Highly conductive ambient-temperature molten salts. Inorg. Chem. 1996, 35, 1168;
24. (c) Seddon, K. R.; Stark, A.; Torres, M.-J. Influence of chloride, water, and organic solvents on the physical properties of ionic liquids. Pure Appl. Chem. 2000, 72, 2275;
25. (d) Owens, G. S.; Abu-Omer, M. M. Comparative kinetic investigations in ionic liquids using the MTO/peroxide system. J. Mol. Catal. 2002, 183A, 2.