Title:
METHOD FOR PREPARING 2-IODO ARYL ETHER UNDER THE ACTION OF ALKALI METAL HYDRIDE
Document Type and Number:
WIPO Patent Application WO/2022/178692
Kind Code:
A1
Abstract:
Disclosed in the present invention is a method for preparing 2-iodo aryl ether under the action of alkali metal hydride: adding alkali metal hydride and phenol to a solvent, then adding 1,2-diiodoarene, and reacting at 0-100℃ to obtain a 2-iodo aryl ether product. The coupling process of the present invention does not require the addition of a transition metal catalyst, and does not cause metal contamination to the product; the method of the present invention can be performed at room temperature and has high functional group compatibility, and solves the problem that existing metal-catalysed coupling to aryl ether reactions need to be performed at a relatively high temperature.
Inventors:
ZHANG SHILEI (CN)
ZHU WENJING (CN)
FANG CHUNHUI (CN)
HU YANWEI (CN)
CHEN XIN (CN)
HUANG JIAWEN (CN)
ZHU WENJING (CN)
FANG CHUNHUI (CN)
HU YANWEI (CN)
CHEN XIN (CN)
HUANG JIAWEN (CN)
Application Number:
PCT/CN2021/077530
Publication Date:
September 01, 2022
Filing Date:
February 23, 2021
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07B41/04; C07C41/16; C07C253/30; C07C255/54
Foreign References:
| CN112979400A | 2021-06-18 | |||
| CN112979497A | 2021-06-18 |
Other References:
WEN SONG YUE ET AL.: "A Concise Synthesis of All Four Possible Benzo[4, 5]furopyridines via Palladium-Mediated Reactions", ORGANIC LETTERS, vol. 4, no. 13, 31 December 2002 (2002-12-31), XP055042429, ISSN: 1523-706, DOI: 10.1021/ol0260425
NARJES FRANK, XUE YAFENG, VON BERG STEFAN, MALMBERG JESPER, LLINAS ANTONIO, OLSSON ROINE I., JIRHOLT JOHAN, GRINDEBACKE HANNA, LEF: "Potent and Orally Bioavailable Inverse Agonists of RORγt Resulting from Structure-Based Design", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 61, no. 17, 13 September 2018 (2018-09-13), US , pages 7796 - 7813, XP055961851, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.8b00783
HUANGGUAN CHEN; JIANWEI HAN; LIMIN WANG: "Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho‐Iodo Diaryl Ethers", ANGEWANDTE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 130, no. 38, 23 August 2018 (2018-08-23), DE , pages 12493 - 12497, XP071376296, ISSN: 0044-8249, DOI: 10.1002/ange.201806405
BAO YONG-SHENG, AGULA BAO, ZHAORIGETU BAO, JIA MEILIN, BAIYIN MENGHE: "One pot synthesis of diarylfurans from aryl esters and PhI(OAc) 2 via palladium-associated iodonium ylides", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 13, no. 14, 1 January 2015 (2015-01-01), pages 4179 - 4182, XP055961849, ISSN: 1477-0520, DOI: 10.1039/C5OB00273G
TIETZE LUTZ F., CHRISTOPH EICHHORST, TIM HUNGERLAND, MARKUS STEINERT: "A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 20, no. 39, 11 August 2014 (2014-08-11), DE, pages 12553 - 12558, XP055961848, ISSN: 0947-6539, DOI: 10.1002/chem.201402961
NARJES FRANK, XUE YAFENG, VON BERG STEFAN, MALMBERG JESPER, LLINAS ANTONIO, OLSSON ROINE I., JIRHOLT JOHAN, GRINDEBACKE HANNA, LEF: "Potent and Orally Bioavailable Inverse Agonists of RORγt Resulting from Structure-Based Design", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 61, no. 17, 13 September 2018 (2018-09-13), US , pages 7796 - 7813, XP055961851, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.8b00783
HUANGGUAN CHEN; JIANWEI HAN; LIMIN WANG: "Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho‐Iodo Diaryl Ethers", ANGEWANDTE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 130, no. 38, 23 August 2018 (2018-08-23), DE , pages 12493 - 12497, XP071376296, ISSN: 0044-8249, DOI: 10.1002/ange.201806405
BAO YONG-SHENG, AGULA BAO, ZHAORIGETU BAO, JIA MEILIN, BAIYIN MENGHE: "One pot synthesis of diarylfurans from aryl esters and PhI(OAc) 2 via palladium-associated iodonium ylides", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 13, no. 14, 1 January 2015 (2015-01-01), pages 4179 - 4182, XP055961849, ISSN: 1477-0520, DOI: 10.1039/C5OB00273G
TIETZE LUTZ F., CHRISTOPH EICHHORST, TIM HUNGERLAND, MARKUS STEINERT: "A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 20, no. 39, 11 August 2014 (2014-08-11), DE, pages 12553 - 12558, XP055961848, ISSN: 0947-6539, DOI: 10.1002/chem.201402961
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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