Title:
SYNTHESIS METHOD FOR DIFLUORODEUTEROMETHOXY(THIO) FUNCTIONAL GROUP-CONTAINING AROMATIC COMPOUND
Document Type and Number:
WIPO Patent Application WO/2018/232777
Kind Code:
A1
Abstract:
A synthesis method for an aromatic compound containing a difluorodeuteromethoxy functional group or a difluorodeuterothio functional group. In the presence of an alkali, a difluorocarbene donor and Ar-(XH)n and heavy water undergo a reaction to produce a deuterated product Ar-(XCF2D)n, the difluorocarbene donor being BrCF2PO(OR)2 or (chlorodifluoromethyl)trimethylsilane or (bromodifluoromethyl)trimethylsilane, and the alkali being selected from Na, K, Li, Mg, Zn, Al, NaH, KH, LiH, LiAlH4, KOD, NaOD, NaOMe, NaOEt, NaOBu, sodium carbonate, potassium carbonate and cesium carbonate. The method has the advantages of cheap and easily available raw materials, simple and mild reaction, high yield, high deuteration rate, and production amplification easiness.
Inventors:
WU YUSHENG (CN)
GENG YANG (CN)
ZOU DAPENG (CN)
LI JINGYA (CN)
NIU CHENGSHAN (CN)
ZHENG MAOLIN (CN)
LIANG APENG (CN)
GENG YANG (CN)
ZOU DAPENG (CN)
LI JINGYA (CN)
NIU CHENGSHAN (CN)
ZHENG MAOLIN (CN)
LIANG APENG (CN)
Application Number:
PCT/CN2017/090937
Publication Date:
December 27, 2018
Filing Date:
June 29, 2017
Export Citation:
Assignee:
TETRANOV PHARMACEUTICAL CO LTD (CN)
International Classes:
C07B59/00; C07C41/16; C07C43/225; C07C253/30
Domestic Patent References:
| WO1994017016A1 | 1994-08-04 |
Foreign References:
| CN106083736A | 2016-11-09 | |||
| US4188405A | 1980-02-12 |
Other References:
YOSSI ZAFRANI ET AL.: "Diethyl Bromodifluoromethylphosphonate: a Highly Efficient and Environmentally Benign Difluorocarbene Precursor", TETRAHEDRON, vol. 65, 3 May 2009 (2009-05-03), pages 5278 - 5283, XP026149872, ISSN: 0040-4020
Z HANG, WEI ET AL.: "N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: A New Difluoromethylation Reagent for S-, N-, and C-Nucleophiles", ORGANIC LETTERS, vol. 11, no. 10, 15 April 2009 (2009-04-15), pages 2109 - 2112, XP055173258, ISSN: 1523-7052
ISMALAJ ERMAL ET AL.: "Direct Electrophilic (Benzenesulfonyl) Difluoromethylthiolation with a Shelf-Stable Reagent", ANGEW. CHEM., vol. 55, 8 March 2015 (2015-03-08), pages 4790 - 4793, XP055555263, ISSN: 1433-7851
Z HANG, WEI ET AL.: "N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: A New Difluoromethylation Reagent for S-, N-, and C-Nucleophiles", ORGANIC LETTERS, vol. 11, no. 10, 15 April 2009 (2009-04-15), pages 2109 - 2112, XP055173258, ISSN: 1523-7052
ISMALAJ ERMAL ET AL.: "Direct Electrophilic (Benzenesulfonyl) Difluoromethylthiolation with a Shelf-Stable Reagent", ANGEW. CHEM., vol. 55, 8 March 2015 (2015-03-08), pages 4790 - 4793, XP055555263, ISSN: 1433-7851
Attorney, Agent or Firm:
CHINA WISPRO INTELLECTUAL PROPERTY LLP. (CN)
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