Regioselective aromatic monobromination of alkyl phenyl ethers with NaClO2, NaBr, Mn(acac)3, and Montmorillonite K10 in dichloromethane

Synthetic Communications

Volumn 28, Issue 4, 1998, Pages 669-676

  Hirano, Masao ^a   Yakabe, Shigetaka ^a   Monobe, Hiroyuki ^a   Morimoto, Takashi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; DICHLOROMETHANE; MANGANESE DERIVATIVE; MONTMORILLONITE; SODIUM BROMIDE; SODIUM CHLORIDE;

ARTICLE; BROMINATION; DRUG CONFORMATION; DRUG SYNTHESIS; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0031929573     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808005939     Document Type: Article

References (37)

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7. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
8. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
9. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
10. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
11. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
12. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
13. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
14. Recently developed aromatic brominations: Ref. 3. Paul, V.; Sudalai, A.; Srinivasan, K. V. Synth. Commun., 1995, 25, 2401. Carreno, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem., 1995, 60, 5328. Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.; Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn., 1994, 67, 1918. Goldberg, Y.; Alper, H. J. Org. Chem., 1993, 58, 3072. Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun., 1992, 22, 1095. Lee, J. G.; Cha, H. T.; Yoon, U. C.; Suh, Y. S.; Kim, K. C.; Park, I. S. Bull. Korean Chem. Soc., 1991, 12, 4. Kajigaeshi, S.; Moriwaki, M.;. Tanaka, T.; Fujisaki, S.; Kakinami, T.; Okamoto, T. J. Chem. Soc., Perkin Trans 1, 1990, 897. Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62, 591. Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Tanaka, T.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn., 1989, 62, 439. Kamigata, N.; Satoh, T.; Yoshida, M.; Matsuyama, H.; Kameyama, M. Bull. Chem. Soc. Jpn., 1988, 61, 2226. Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem., 1988. 53, 2093.
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