Title:
FLUOROALKYLATING AGENT
Document Type and Number:
WIPO Patent Application WO/2015/199109
Kind Code:
A1
Abstract:
[Problem] To provide an industrially suitable fluoroalkylating agent and uses thereof. [Solution] A fluoroalkylating agent represented by general formula (1) (wherein R1 represents a C1–C8 fluoroalkyl group; R2 and R3 independently represent C1–C12 alkyl groups or the like; Y1–Y4 independently represent hydrogen atoms, halogen atoms, or the like; and X– represents a monovalent anion). A compound represented by general formula (3): R4-S-R1, with a C1–C8 fluoroalkyl group introduced therein, can easily be obtained by reacting a compound represented by general formula (2): R4-S-Z (wherein R4 represents a hydrocarbon group, or the like, and Z represents a leaving group) with a compound represented by general formula (1).
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Inventors:
KAWAZOE KENTARO (JP)
YOSHIOKA KOTARO (JP)
YOSHIOKA KOTARO (JP)
Application Number:
PCT/JP2015/068127
Publication Date:
December 30, 2015
Filing Date:
June 24, 2015
Export Citation:
Assignee:
IHARA CHEMICAL IND CO (JP)
KUMIAI CHEMICAL INDUSTRY CO (JP)
KUMIAI CHEMICAL INDUSTRY CO (JP)
International Classes:
C07D235/10; C07C29/38; C07C31/38; C07C319/14; C07C323/12; C07B61/00
Domestic Patent References:
| WO2013157229A1 | 2013-10-24 | |||
| WO2012129384A2 | 2012-09-27 | |||
| WO2001060803A1 | 2001-08-23 |
Foreign References:
| CN102229569A | 2011-11-02 |
Other References:
SURYA PRAKASH, G. K. ET AL.: "Alkoxide- and Hydroxide-Induced Nucleophilic Trifluoromethylation Using Trifluoromethyl Sulfone or Sulfoxide", ORGANIC LETTERS, vol. 5, no. 18, 2003, pages 3253 - 3256, XP055248585, ISSN: 1523-7060
CHERKUPALLY, P. ET AL.: "Alkoxide-induced nucleophilic trifluoromethylation using diethyl trifluoromethylphosphonate", TETRAHEDRON LETTERS, vol. 51, no. 2, 2010, pages 252 - 255, XP027259027, ISSN: 0040-4039
LARINA, L. I. ET AL.: "Investigation of benzimidazoles. II. The influence of substituents and solvents on the 1H and 13C NMR chemical shifts of 2-substituted 1,3- dimethylbenzimidazolium perchlorates", ORGANIC MAGNETIC RESONANCE, vol. 17, no. 1, 1981, pages 1 - 5, XP055248593
KRASOVSKIY, A. L. ET AL.: "Synthesis of CF3- containing beta-hetaryl-substituted enones", RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION, vol. 52, no. 8, 2003, pages 1791 - 1796, XP019224816, ISSN: 1573-9171
EAPEN, K. C. ET AL.: "Synthesis of some benzimidazoles containing 2-perfluoro substituents", JOURNAL OF FLUORINE CHEMISTRY, vol. 18, no. 3, 1981, pages 243 - 257, XP055248600, ISSN: 0022-1139
KUZNETSOV, V. S.: "Polarographic study of ring- substituted naphtho[2,3-d]imidazole-4,9-diones and their quaternary salts", ZHURNAL OBSHCHEI KHIMII, vol. 37, no. 8, 1967, pages 1802 - 1809, XP008183855
OGRETIR, C. ET AL.: "Benzimidazole studies. IV. Investigation of the nitration kinetics of some benzimidazole derivatives and Hammett relationships", CHIMICA ACTA TURC ICA, vol. 14, no. 2, 1986, pages 199 - 211, XP008183857
KUZNETSOV, V. S. ET AL.: "Heterocyclic derivatives of substituted 1,4-naphthoquinones. VI. Derivatives of naphtho[2,3-d]imidazole-4,9- dione", ZHURNAL ORGANICHESKOI KHIMII, vol. 3, no. 2, 1967, pages 393 - 402, XP008183856
FILE REGISTRY ON STN , RN 64085-79-6, ED ENTERED STN, 16 November 1984 (1984-11-16)
CHERKUPALLY, P. ET AL.: "Alkoxide-induced nucleophilic trifluoromethylation using diethyl trifluoromethylphosphonate", TETRAHEDRON LETTERS, vol. 51, no. 2, 2010, pages 252 - 255, XP027259027, ISSN: 0040-4039
LARINA, L. I. ET AL.: "Investigation of benzimidazoles. II. The influence of substituents and solvents on the 1H and 13C NMR chemical shifts of 2-substituted 1,3- dimethylbenzimidazolium perchlorates", ORGANIC MAGNETIC RESONANCE, vol. 17, no. 1, 1981, pages 1 - 5, XP055248593
KRASOVSKIY, A. L. ET AL.: "Synthesis of CF3- containing beta-hetaryl-substituted enones", RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION, vol. 52, no. 8, 2003, pages 1791 - 1796, XP019224816, ISSN: 1573-9171
EAPEN, K. C. ET AL.: "Synthesis of some benzimidazoles containing 2-perfluoro substituents", JOURNAL OF FLUORINE CHEMISTRY, vol. 18, no. 3, 1981, pages 243 - 257, XP055248600, ISSN: 0022-1139
KUZNETSOV, V. S.: "Polarographic study of ring- substituted naphtho[2,3-d]imidazole-4,9-diones and their quaternary salts", ZHURNAL OBSHCHEI KHIMII, vol. 37, no. 8, 1967, pages 1802 - 1809, XP008183855
OGRETIR, C. ET AL.: "Benzimidazole studies. IV. Investigation of the nitration kinetics of some benzimidazole derivatives and Hammett relationships", CHIMICA ACTA TURC ICA, vol. 14, no. 2, 1986, pages 199 - 211, XP008183857
KUZNETSOV, V. S. ET AL.: "Heterocyclic derivatives of substituted 1,4-naphthoquinones. VI. Derivatives of naphtho[2,3-d]imidazole-4,9- dione", ZHURNAL ORGANICHESKOI KHIMII, vol. 3, no. 2, 1967, pages 393 - 402, XP008183856
FILE REGISTRY ON STN , RN 64085-79-6, ED ENTERED STN, 16 November 1984 (1984-11-16)
Attorney, Agent or Firm:
SHA Takuho (JP)
謝 卓峰 (JP)
謝 卓峰 (JP)
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