Title:
PRODUCTION METHOD FOR CYCLOALKYL(TRIFLUOROMETHYL)BENZENE
Document Type and Number:
WIPO Patent Application WO/2019/013126
Kind Code:
A1
Abstract:
The present invention provides an industrially excellent method for highly efficiently producing a cycloalkyl(trifluoromethyl)benzene without any complicated step and through a small number of steps. A halogen-substituted trifluoromethylbenzene is reacted with magnesium metal to convert the compound into a Grignard reagent. The Grignard reagent is cross-coupled with a cycloalkyl halide in the presence of an iron salt or a cobalt salt at a reaction temperature of 60-80°C to produce a cycloalkyl(trifluoromethyl)benzene.
Inventors:
NAKATANI JIRO (JP)
Application Number:
PCT/JP2018/025696
Publication Date:
January 17, 2019
Filing Date:
July 06, 2018
Export Citation:
Assignee:
TORAY FINECHEMICALS CO LTD (JP)
International Classes:
C07C17/26; C07C22/08; C07B61/00
Domestic Patent References:
| WO2010001640A1 | 2010-01-07 | |||
| WO2010011316A1 | 2010-01-28 | |||
| WO2013113915A1 | 2013-08-08 |
Foreign References:
| JP2013518106A | 2013-05-20 | |||
| JP2011001369A | 2011-01-06 | |||
| JP2016121121A | 2016-07-07 |
Other References:
CZAPLIK, W.. M. ET AL.: "Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling", ANGEW. CHEM. INT. ED., vol. 48, 2009, pages 607 - 610, XP002542136
LI, Z. ET AL.: "Iron-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl chlorides with aryl bromides", ORG. BIOMOL. CHEM., vol. 14, 2016, pages 3314 - 3321, XP055564505
HEDSTROEM, A. ET AL.: "Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study", CHEM. EUR. J., vol. 17, 2011, pages 11991 - 11993, XP055564512
TANAKA, YOSHIE ET AL.: "Development of efficient structure conversion reaction of aromatic compounds aiming not to use rare-metal", RESEARCH REPORTS OF INDUSTRIAL TECHNOLOGY CENTER OF WAKAYAMA, vol. 23, 2011, pages 25, XP009518237, ISSN: 1340-5799
JOURNAL OF AMERICAN CHEMISTRY SOCIETY, vol. 126, 2004, pages 3686 - 3687
ORGANIC LETTERS, vol. 14, no. 4, 2012, pages 1066 - 1069
CHEMISTRY LETTERS, vol. 40, 2011, pages 983 - 985
CHEMISTRY LETTER, vol. 40, 2011, pages 1030 - 1032
SENGUPTA ET AL.: "An Efficient Scale-Up Process for the Preparation of the APD334 Precursor 4-Chloromethyl-1-cyclopentyl-2-(trifluoromethyl)benzene", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 19, no. 6, 25 May 2015 (2015-05-25), pages 618 - 623, XP055752890
See also references of EP 3653594A4
LI, Z. ET AL.: "Iron-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl chlorides with aryl bromides", ORG. BIOMOL. CHEM., vol. 14, 2016, pages 3314 - 3321, XP055564505
HEDSTROEM, A. ET AL.: "Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study", CHEM. EUR. J., vol. 17, 2011, pages 11991 - 11993, XP055564512
TANAKA, YOSHIE ET AL.: "Development of efficient structure conversion reaction of aromatic compounds aiming not to use rare-metal", RESEARCH REPORTS OF INDUSTRIAL TECHNOLOGY CENTER OF WAKAYAMA, vol. 23, 2011, pages 25, XP009518237, ISSN: 1340-5799
JOURNAL OF AMERICAN CHEMISTRY SOCIETY, vol. 126, 2004, pages 3686 - 3687
ORGANIC LETTERS, vol. 14, no. 4, 2012, pages 1066 - 1069
CHEMISTRY LETTERS, vol. 40, 2011, pages 983 - 985
CHEMISTRY LETTER, vol. 40, 2011, pages 1030 - 1032
SENGUPTA ET AL.: "An Efficient Scale-Up Process for the Preparation of the APD334 Precursor 4-Chloromethyl-1-cyclopentyl-2-(trifluoromethyl)benzene", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 19, no. 6, 25 May 2015 (2015-05-25), pages 618 - 623, XP055752890
See also references of EP 3653594A4
Attorney, Agent or Firm:
SEIRYU PATENT PROFESSIONAL CORPORATION et al. (JP)
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