Title:
METHOD FOR PRODUCING MERCAPTOPHENOL COMPOUND AND INTERMEDIATE OF SAID COMPOUND
Document Type and Number:
WIPO Patent Application WO/2019/167814
Kind Code:
A1
Abstract:
[Problem] To provide: a production method whereby a mercaptophenol compound is obtained using an industrially preferable reaction for sulfur atom introduction; and an intermediate of the mercaptophenol compound.
[Solution] A method for producing a mercaptophenol compound via a phenyl mercaptocarbamate compound as an intermediate, the method comprising using a phenol compound as a starting material to produce a phenyl carbamate compound and thereafter reacting the phenyl carbamate compound with sulfur monochloride to position-selectively introduce a sulfur atom.
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Inventors:
SAMBAI KAZUHIRO (JP)
Application Number:
PCT/JP2019/006674
Publication Date:
September 06, 2019
Filing Date:
February 22, 2019
Export Citation:
Assignee:
KUMIAI CHEMICAL INDUSTRY CO (JP)
International Classes:
C07C321/26; C07C271/44; C07C319/06; C07C319/12; C07C319/24; C07C321/28
Domestic Patent References:
| WO2015122396A1 | 2015-08-20 | |||
| WO2013157229A1 | 2013-10-24 | |||
| WO2013111864A1 | 2013-08-01 | |||
| WO2015025826A1 | 2015-02-26 | |||
| WO2015122396A1 | 2015-08-20 |
Foreign References:
| DE961042C | 1957-03-28 | |||
| JP2002260730A | 2002-09-13 | |||
| EP0006990A1 | 1980-01-23 | |||
| DE2119518A1 | 1972-10-26 | |||
| DE1139113B | 1962-11-08 | |||
| JP2016084346A | 2016-05-19 | |||
| CN107286057A | 2017-10-24 |
Other References:
SUN, X. ET AL.: "Room-temperature Pd-catalyzed C-H chlorination by weak coordination: one-pot synthesis of 2-chlorophenols with excellent regioselectivity", CHEMICAL COMMUNICATIONS, vol. 50, no. 10, 2014, pages 1262 - 1264, XP055634798, ISSN: 1359-7345, DOI: 10.1039/C3CC47431C
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-39-3
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-40-6
SUN, X. ET AL.: "Pd(II) catalyzed ortho C-H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents", CHEMICAL COMMUNICATIONS, vol. 51, no. 49, 2015, pages 10014 - 10017, XP055634801, ISSN: 1359-7345, DOI: 10.1039/C5CC02533H
JOHN, A. ET AL.: "Palladium Catalyzed C-H Functionalization of 0-Arylcarbamates: Selective ortho-Bromination Using NBS", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 13, 2012, pages 5600 - 5605, XP055428085, ISSN: 0022-3263, DOI: 10.1021/jo300713h
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-41-7
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-43-9
WESSELY, F.SILHAN, W.POLANSKY, 0. E.: "Preparation of m-hydroxyphenylsulfonic acids and m-hydroxythiophenol", MONATSHEFTE FUER CHEMIE, vol. 99, 1968, pages 2048 - 2058
WESSELY, F.SWOBODA, J.SCHMIDT, G.: "Action of thiols and sulfinic acids on quinol acetates. II", MONATSHEFTE FUER CHEMIE, vol. 91, 1960, pages 57 - 78
"Shin Jikkenkagaku Koza (New Experimental Chemistry Course) 9 Bunsekikagaku (Analytical Chemistry) II", 1977, SHINGO IIZUMI, MARUZEN CO., LTD, pages: 86 - 112
"Jikkenkagaku Koza (Experimental Chemistry Course) 20-1 Bunsekikagaku (Analytical Chemistry", 2007, SEISHIRO MURATA, MARUZEN CO., LTD, pages: 130 - 151
"Jikkenkagaku Koza (Experimental Chemistry Course) 4 Netsu, Atsuryoku (Heat and Pressure", 1992, KUMAO EBIHARA, MARUZEN CO., LTD, pages: 57 - 93
"Jikkenkagaku Koza (Experimental Chemistry Course) 6 Ondo-Netsu, Atsuryoku (Temperature and Heat and Pressure", 2005, SEISHIRO MURATA, MARUZEN CO., LTD, pages: 203 - 205
See also references of EP 3760613A4
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-39-3
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-40-6
SUN, X. ET AL.: "Pd(II) catalyzed ortho C-H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents", CHEMICAL COMMUNICATIONS, vol. 51, no. 49, 2015, pages 10014 - 10017, XP055634801, ISSN: 1359-7345, DOI: 10.1039/C5CC02533H
JOHN, A. ET AL.: "Palladium Catalyzed C-H Functionalization of 0-Arylcarbamates: Selective ortho-Bromination Using NBS", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 13, 2012, pages 5600 - 5605, XP055428085, ISSN: 0022-3263, DOI: 10.1021/jo300713h
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-41-7
DATABASE CAS [online] 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 36552-43-9
WESSELY, F.SILHAN, W.POLANSKY, 0. E.: "Preparation of m-hydroxyphenylsulfonic acids and m-hydroxythiophenol", MONATSHEFTE FUER CHEMIE, vol. 99, 1968, pages 2048 - 2058
WESSELY, F.SWOBODA, J.SCHMIDT, G.: "Action of thiols and sulfinic acids on quinol acetates. II", MONATSHEFTE FUER CHEMIE, vol. 91, 1960, pages 57 - 78
"Shin Jikkenkagaku Koza (New Experimental Chemistry Course) 9 Bunsekikagaku (Analytical Chemistry) II", 1977, SHINGO IIZUMI, MARUZEN CO., LTD, pages: 86 - 112
"Jikkenkagaku Koza (Experimental Chemistry Course) 20-1 Bunsekikagaku (Analytical Chemistry", 2007, SEISHIRO MURATA, MARUZEN CO., LTD, pages: 130 - 151
"Jikkenkagaku Koza (Experimental Chemistry Course) 4 Netsu, Atsuryoku (Heat and Pressure", 1992, KUMAO EBIHARA, MARUZEN CO., LTD, pages: 57 - 93
"Jikkenkagaku Koza (Experimental Chemistry Course) 6 Ondo-Netsu, Atsuryoku (Temperature and Heat and Pressure", 2005, SEISHIRO MURATA, MARUZEN CO., LTD, pages: 203 - 205
See also references of EP 3760613A4
Attorney, Agent or Firm:
SHA Takuho (JP)
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