JP2018514538A5 - - Google Patents
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- Publication number
- JP2018514538A5 JP2018514538A5 JP2017556167A JP2017556167A JP2018514538A5 JP 2018514538 A5 JP2018514538 A5 JP 2018514538A5 JP 2017556167 A JP2017556167 A JP 2017556167A JP 2017556167 A JP2017556167 A JP 2017556167A JP 2018514538 A5 JP2018514538 A5 JP 2018514538A5
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- process according
- chlorobenzene
- xylene
- toluene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- -1 alkali metal cation Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 6
- 239000012025 fluorinating agent Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000003444 phase transfer catalyst Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- LYWKAJZTPLXHEM-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;chloride Chemical compound [Cl-].CCN(CC)C(N(CC)CC)=[N+](CC)CC LYWKAJZTPLXHEM-UHFFFAOYSA-M 0.000 claims 2
- WKHWMSFGRUVCNP-UHFFFAOYSA-M bis(dimethylamino)methylidene-dimethylazanium;chloride Chemical compound [Cl-].CN(C)C(N(C)C)=[N+](C)C WKHWMSFGRUVCNP-UHFFFAOYSA-M 0.000 claims 2
- 229940117389 dichlorobenzene Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 2
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims 2
- PUIREZSBEHKZON-UHFFFAOYSA-N 5-chloro-1h-pyrazole-4-carbonyl chloride Chemical compound ClC(=O)C=1C=NNC=1Cl PUIREZSBEHKZON-UHFFFAOYSA-N 0.000 claims 1
- JFQHKAZLEJKYFD-UHFFFAOYSA-N 5-fluoro-1H-pyrazole-4-carbonyl fluoride Chemical compound FC1=C(C=NN1)C(=O)F JFQHKAZLEJKYFD-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- CASUWTAPYGBPLM-UHFFFAOYSA-M bis(dibutylamino)methylidene-dibutylazanium;chloride Chemical compound [Cl-].CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CASUWTAPYGBPLM-UHFFFAOYSA-M 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 235000003270 potassium fluoride Nutrition 0.000 claims 1
- 239000011698 potassium fluoride Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 0 *c1n[n](*)c(F)c1C(F)=O Chemical compound *c1n[n](*)c(F)c1C(F)=O 0.000 description 1
- CXMYJZYKGYORER-UHFFFAOYSA-N 3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carbonyl fluoride Chemical compound CN1N=C(C(F)F)C(C(F)=O)=C1F CXMYJZYKGYORER-UHFFFAOYSA-N 0.000 description 1
- CHYVHFOEFHHBJB-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole-4-carbonyl chloride Chemical compound CN1N=C(C(F)F)C(C(Cl)=O)=C1Cl CHYVHFOEFHHBJB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15290112 | 2015-04-29 | ||
| EP15290112.0 | 2015-04-29 | ||
| PCT/EP2016/059462 WO2016174121A1 (en) | 2015-04-29 | 2016-04-28 | Method for preparing 5-fluoro-1h-pyrazole-4-carbonyl fluorides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018514538A JP2018514538A (ja) | 2018-06-07 |
| JP2018514538A5 true JP2018514538A5 (cg-RX-API-DMAC7.html) | 2019-12-12 |
| JP6691925B2 JP6691925B2 (ja) | 2020-05-13 |
Family
ID=53189745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556167A Active JP6691925B2 (ja) | 2015-04-29 | 2016-04-28 | ５−フルオロ−１ｈ−ピラゾール−４−カルボニルフルオリドの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10125103B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3288923B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6691925B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102585411B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107531640B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112017022808B1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK3288923T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2781780T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL255256B (cg-RX-API-DMAC7.html) |
| MX (1) | MX390887B (cg-RX-API-DMAC7.html) |
| TW (1) | TWI705055B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016174121A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114621178B (zh) * | 2022-03-23 | 2023-10-13 | 内蒙古源宏精细化工有限公司 | 一种氟代碳酸乙烯酯的制备工艺 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19544800A1 (de) | 1995-12-01 | 1997-06-05 | Bayer Ag | Verfahren zur Herstellung von 1,3-Dimethyl-5-fluor-pyrazol-4-carboxaniliden |
| DE19942374A1 (de) * | 1998-11-30 | 2000-05-31 | Solvay Fluor & Derivate | Verfahren zur Herstellung von Säurefluoriden aus Säurechloriden |
| DE102005044451A1 (de) * | 2005-09-17 | 2007-03-22 | Bayer Cropscience Gmbh | Verfahren zum Herstellen von 5-Fluor-1,3-dialkyl-1H-pyrazol-4-carbonsäurefluoriden |
| DE102007002674A1 (de) | 2007-01-18 | 2008-07-24 | Bayer Cropscience Ag | Verfahren zum Herstellen von substituierten Pyrazolcarbonsäurechloriden |
| DE102009003025A1 (de) | 2009-05-12 | 2010-11-18 | Ball Packaging Europe Gmbh | Verfahren zum Befüllen von Lebenmittelbehältern |
| AR076839A1 (es) * | 2009-05-15 | 2011-07-13 | Bayer Cropscience Ag | Derivados fungicidas de pirazol carboxamidas |
| EP2325173A1 (de) | 2009-11-19 | 2011-05-25 | Bayer CropScience AG | Verfahren zum Herstellen von 5-Fluor-1-alkyl-3-fluoralkyl-1H-pyrazol-4-carbonsäurechloriden |
| DK2560961T3 (en) | 2010-04-23 | 2017-02-20 | Bayer Ip Gmbh | METHOD FOR PREPARING 5-FLUORO-1-ALKYL-3-FLUORALKYL-1H-PYRAZOL-4-CARBOXYLYRIC CHLORIDE AND FLUORIDES |
| US20130296383A1 (en) * | 2010-11-15 | 2013-11-07 | Bayer Intellectual Property Gmbh | Decahydro-1,4-methanonaphthalen carboxamides |
| WO2012065947A1 (en) * | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazolecarboxamides |
-
2016
- 2016-04-27 TW TW105113149A patent/TWI705055B/zh active
- 2016-04-28 MX MX2017013632A patent/MX390887B/es unknown
- 2016-04-28 BR BR112017022808-4A patent/BR112017022808B1/pt active IP Right Grant
- 2016-04-28 CN CN201680024155.6A patent/CN107531640B/zh active Active
- 2016-04-28 ES ES16721748T patent/ES2781780T3/es active Active
- 2016-04-28 WO PCT/EP2016/059462 patent/WO2016174121A1/en not_active Ceased
- 2016-04-28 KR KR1020177034297A patent/KR102585411B1/ko active Active
- 2016-04-28 DK DK16721748.8T patent/DK3288923T3/da active
- 2016-04-28 JP JP2017556167A patent/JP6691925B2/ja active Active
- 2016-04-28 US US15/569,681 patent/US10125103B2/en active Active
- 2016-04-28 EP EP16721748.8A patent/EP3288923B1/en active Active
-
2017
- 2017-10-25 IL IL255256A patent/IL255256B/en active IP Right Grant
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