Mild and efficient conversion of trifluoromethylarenes into tribromomethylarenes using boron tribromide

[1] Dolbier, W. R., Jr., & Beach, W. F. (2003). Parylene-AF4: a polymer with exceptional dielectric and thermal properties. Journal of Fluorine Chemistry, 122, 97–104. DOI: 10.1016/S0022-1139(03)00100-3. http://dx.doi.org/10.1016/S0022-1139(03)00100-310.1016/S0022-1139(03)00100-3Search in Google Scholar

[2] Dolbier, W. R., Jr., Duan, J.-X., Abboud, K. A., & Ameduri, B. (2000a). Synthesis and reactivity of a novel, dimeric derivative of octafluoro[2.2]paracyclophane. A new source of trifluoromethyl radicals. Journal of the American Chemical Society, 122, 12083–12086. DOI: 10.1021/ja001934q. http://dx.doi.org/10.1021/ja001934q10.1021/ja001934qSearch in Google Scholar

[3] Dolbier, W. R., Jr., Duan, J. X., & Roche, A. J. (2000b). A novel, non-high-dilution method for preparation of 1,1,2,2,9, 9,10,10-octafluoro[2.2]paracyclophane. Organic Letters, 2, 1867–1869. DOI: 10.1021/ol005943f. http://dx.doi.org/10.1021/ol005943f10.1021/ol005943fSearch in Google Scholar PubMed

[4] Dolbier, W. R., Jr., Rong, X. X., Xu, Y., & Beach, W. F. (1997). A new and practical synthesis of octafluoro[2.2]paracyclophane. Journal of Organic Chemistry, 62, 7500–7502. DOI: 10.1021/jo970927. http://dx.doi.org/10.1021/jo970927qSearch in Google Scholar

[5] Hausladen, M. C., Huang B. G., & Tang, D. Y. (1999). U.S. Patent No. 5,866,709. Washington D. C.: U.S. Patent and Trademark Office. Search in Google Scholar

[6] Hunter, W. H., & Edgar, D. E. (1932). Carbon tetrabromide as a brominating agent. Journal of the American Chemical Society, 54, 2025–2028. DOI: 10.1021/ja01344a049. http://dx.doi.org/10.1021/ja01344a04910.1021/ja01344a049Search in Google Scholar

[7] Jones, R. G. (1947). Ortho and para substituted derivatives of benzotrifluoride. Journal of the American Chemical Society, 69, 2346–2350. DOI: 10.1021/ja01202a028. http://dx.doi.org/10.1021/ja01202a02810.1021/ja01202a028Search in Google Scholar PubMed

[8] Kardash, I. E., Pebalk, A. V., Chvalun, S. N., & Mailyan, K. A. (2006). Russian Patent No. 2,268,900. Moscow: Russian Patent & Trademark Office. Search in Google Scholar

[9] Liang, J. C., & Kumar, S. (1987). The synthesis and liquid crystal behavior of p-benzotrifluoride compounds I. Molecular Crystals & Liquid Crystals, 142, 77–84. DOI: 10.1080/00268948708084594. http://dx.doi.org/10.1080/0026894870808459410.1080/00268948708084594Search in Google Scholar

[10] Malichenko, B. F., Alyabeva, G. I., & Kulik, V. F. (1967). Reaction of aluminum halides with m-and p-bis(trifluoromethyl) benzene. Zhurnal Obshchei Khimii, 37, 1626–1631. Search in Google Scholar

[11] Markarian, M. (1952). Trifluoromethyl substituted biphenyls and diphenyl ethers. Journal of the American Chemical Society, 74, 1858–1859. DOI: 10.1021/ja01127a515. http://dx.doi.org/10.1021/ja01127a51510.1021/ja01127a515Search in Google Scholar

[12] Mataka, S., Kurisu, M., Takahashi, K., & Tashiro, M. (1984). The bromination of methylarenes with NBS by irradiation using a tungsten lamp. Preparation of benzotribromides. Chemistry Letters, 13, 1969–1972. DOI: 10.1246/cl.1984.1969. http://dx.doi.org/10.1246/cl.1984.196910.1246/cl.1984.1969Search in Google Scholar

[13] Mataka, S., Liu, G.-B., Sawada, T., Kurisu, M., & Tashiro, M. (1994). Photothermal side-chain bromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide. Bulletin of the Chemical Society of Japan, 67, 1113–1119. DOI: 10.1246/bcsj.67.1113. http://dx.doi.org/10.1246/bcsj.67.111310.1246/bcsj.67.1113Search in Google Scholar

[14] Mataka, S., Liu, G. B., & Tashiro, M. (1995). Palladium(0) complex-catalyzed debrominative coupling of (tribromomethyl)-and (dibromomethyl)benzenes to diarylacetylenes and 1,2-diarylethenes. Synthesis, 2, 133–136. DOI: 10.1055/s-1995-3878. http://dx.doi.org/10.1055/s-1995-387810.1055/s-1995-3878Search in Google Scholar

[15] Myers, R. H., Hobbs, M. E., & Gross, P. M. (1954). Regularities in the densities of dilute solutions of some monochlorobenzotrihalides. Journal of the American Chemical Society, 76, 4737–4739. DOI: 10.1021/ja01647a077. http://dx.doi.org/10.1021/ja01647a07710.1021/ja01647a077Search in Google Scholar

[16] Petracek, F. J., & Zechmeister, L. (1952). Stereoisomeric phytofluenes. Journal of the American Chemical Society, 74, 184–186. DOI: 10.1021/ja01121a047. http://dx.doi.org/10.1021/ja01121a04710.1021/ja01121a047Search in Google Scholar

[17] Qiu, G. X. (2004). China Patent No. 1,465,561. Beijing: State Intellectual Property Office of the P. R. China. Search in Google Scholar

[18] Roche, A. J., Duan, J. X., Dolbier, W. R., Jr., & Abboud, K. A. (2001). The first synthesis and characterization of both diastereomers of a di[2.2]paracyclophane: 4,4′-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane). Journal of Organic Chemistry, 66, 7055–7058. DOI: 10.1021/jo0157775. http://dx.doi.org/10.1021/jo015777510.1021/jo0157775Search in Google Scholar PubMed

[19] Surya Prakash, G. K., Hu, J., Simon, J., Bellew, D. R., & Olah, G. A. (2004). Preparation of α,α-difluoroalkanesulfonic acids. Journal of Fluorine Chemistry, 125, 595–601. DOI: 10.1016/j.jfluchem.2003.11.031. http://dx.doi.org/10.1016/j.jfluchem.2003.11.03110.1016/j.jfluchem.2003.11.031Search in Google Scholar

[20] Takahashi, A., Satsu, Y., Nakai, H., Yefimovich, K. I., Vladimirovich, P. A., Nicolaevich, C. S., & Andranikovich, M. K. (2003). World Patent No. 2,003,011,951. Geneva: World Intellectual Property Organization. Search in Google Scholar

[21] Yagupoľskii, L. M., & Kondratenko, N. V. (1969). Tris(trifluoromethyl) esters of arylorthothiocarboxylic and orthothiocarbonic acids. Zhurnal Obshchei Khimii, 39, 1755–1759. Search in Google Scholar

[22] Zhang, Y. H., Kazutaka, S., & Hisashi, Y. (2005). Lewis acid catalyzed highly selective halogenation of aromatic compounds. Synlett, 18, 2837–2842. DOI: 10.1055/s-2005-918919. 10.1055/s-2005-918919Search in Google Scholar

[23] Zhu, S. Z. (2001). China Patent No. 1,295,996. Beijing: State Intellectual Property Office of the P. R. China. Search in Google Scholar