TWI705055B - 製備5-氟-1h-吡唑-4-羰基氟化物之方法 - Google Patents
製備5-氟-1h-吡唑-4-羰基氟化物之方法 Download PDFInfo
- Publication number
- TWI705055B TWI705055B TW105113149A TW105113149A TWI705055B TW I705055 B TWI705055 B TW I705055B TW 105113149 A TW105113149 A TW 105113149A TW 105113149 A TW105113149 A TW 105113149A TW I705055 B TWI705055 B TW I705055B
- Authority
- TW
- Taiwan
- Prior art keywords
- chloride
- xylene
- pyrazole
- methyl
- phosphonium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- JFQHKAZLEJKYFD-UHFFFAOYSA-N 5-fluoro-1H-pyrazole-4-carbonyl fluoride Chemical class FC1=C(C=NN1)C(=O)F JFQHKAZLEJKYFD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 16
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 15
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 239000011698 potassium fluoride Substances 0.000 claims description 10
- -1 alkali metal cation Chemical class 0.000 claims description 9
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 7
- 229940117389 dichlorobenzene Drugs 0.000 claims description 7
- 229940078552 o-xylene Drugs 0.000 claims description 7
- 239000012025 fluorinating agent Substances 0.000 claims description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 6
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 6
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 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 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- PUIREZSBEHKZON-UHFFFAOYSA-N 5-chloro-1h-pyrazole-4-carbonyl chloride Chemical class ClC(=O)C=1C=NNC=1Cl PUIREZSBEHKZON-UHFFFAOYSA-N 0.000 abstract description 8
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract description 7
- 239000012454 non-polar solvent Substances 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000002798 polar solvent Substances 0.000 description 8
- 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 7
- 241000208340 Araliaceae Species 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 6
- 235000003140 Panax quinquefolius Nutrition 0.000 description 6
- 235000008434 ginseng Nutrition 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 0 *c1n[n](*)c(F)c1C(F)=O Chemical compound *c1n[n](*)c(F)c1C(F)=O 0.000 description 4
- 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 4
- 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 description 4
- 238000004821 distillation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229940113088 dimethylacetamide Drugs 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WQOCRQDVKIZUMX-UHFFFAOYSA-N 1h-pyrazole-4-carbonyl fluoride Chemical compound FC(=O)C=1C=NNC=1 WQOCRQDVKIZUMX-UHFFFAOYSA-N 0.000 description 2
- QDEGJIIFYAYGCK-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole-4-carbonyl fluoride Chemical compound CN1N=C(C(F)F)C(C(F)=O)=C1Cl QDEGJIIFYAYGCK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- PGMXFQIJTPTXON-UHFFFAOYSA-N (dihexylamino)-(dimethylamino)phosphanium bromide Chemical compound [Br-].CCCCCCN([PH2+]N(C)C)CCCCCC PGMXFQIJTPTXON-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WIWMMJPXRWAZBB-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=NN(C)C(Cl)=C1C(Cl)=O WIWMMJPXRWAZBB-UHFFFAOYSA-N 0.000 description 1
- FSLWXANTEMFPRQ-UHFFFAOYSA-N 5-fluoro-1,3-dimethylpyrazole-4-carbonyl fluoride Chemical compound CC1=NN(C)C(F)=C1C(F)=O FSLWXANTEMFPRQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical class N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CJTDRDJUGRBDKP-UHFFFAOYSA-N bis(dibutylamino)methylidene-dibutylazanium Chemical compound CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CJTDRDJUGRBDKP-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- LSKVBJHJMLFTDB-UHFFFAOYSA-N chloro(methyl)phosphane Chemical compound CPCl LSKVBJHJMLFTDB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- AEIDGXGANVZOLL-UHFFFAOYSA-N diethylamino(dimethylamino)phosphanium;bromide Chemical compound [Br-].CCN(CC)[PH2+]N(C)C AEIDGXGANVZOLL-UHFFFAOYSA-N 0.000 description 1
- WRRGEPKWIVTPBR-UHFFFAOYSA-N diethylaminophosphanium chloride Chemical compound [Cl-].C(C)N(CC)[PH3+] WRRGEPKWIVTPBR-UHFFFAOYSA-N 0.000 description 1
- QCMNWZDTWSLXMJ-UHFFFAOYSA-N diethylaminophosphanium;bromide Chemical compound [Br-].CCN([PH3+])CC QCMNWZDTWSLXMJ-UHFFFAOYSA-N 0.000 description 1
- HFJXZPZCSVOZNL-UHFFFAOYSA-N dimethylaminophosphanium;bromide Chemical compound [Br-].CN(C)[PH3+] HFJXZPZCSVOZNL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- BJAOWHVROIMDMK-UHFFFAOYSA-N hexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[PH2+]CCCCCC BJAOWHVROIMDMK-UHFFFAOYSA-N 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- VBKNTGMWIPUCRF-UHFFFAOYSA-M potassium;fluoride;hydrofluoride Chemical compound F.[F-].[K+] VBKNTGMWIPUCRF-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- RJELOMHXBLDMDB-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC RJELOMHXBLDMDB-UHFFFAOYSA-M 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N29/00—Biocides, pest repellants or attractants, or plant growth regulators containing halogenated hydrocarbons
- A01N29/04—Halogen directly attached to a carbocyclic ring system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15290112 | 2015-04-29 | ||
| EP15290112.0 | 2015-04-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201704215A TW201704215A (zh) | 2017-02-01 |
| TWI705055B true TWI705055B (zh) | 2020-09-21 |
Family
ID=53189745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW105113149A TWI705055B (zh) | 2015-04-29 | 2016-04-27 | 製備5-氟-1h-吡唑-4-羰基氟化物之方法 |
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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031212A1 (de) * | 2005-09-17 | 2007-03-22 | Bayer Cropscience Ag | Verfahren zum herstellen von 5-fluor-1,3-dialkyl-1h-pyrazol-4-carbonsäurefluoriden |
| WO2010130767A2 (en) * | 2009-05-15 | 2010-11-18 | Bayer Cropscience Ag | Fungicide pyrazole carboxamides derivatives |
Family Cites Families (8)
| 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 |
| 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 |
| 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 |
| CN103140477B (zh) * | 2010-04-23 | 2015-07-15 | 拜耳知识产权股份有限公司 | 制备5-氟-1-烷基-3-氟烷基-1h-吡唑-4-酰氯和酰氟的方法 |
| BR112013011936A2 (pt) * | 2010-11-15 | 2017-11-07 | Bayer Ip Gmbh | deca-hidro -1, 4-metanonaftaleno - carboxamidas |
| AR083876A1 (es) * | 2010-11-15 | 2013-03-27 | Bayer Cropscience Ag | 5-halogenopirazolcarboxamidas |
-
2016
- 2016-04-27 TW TW105113149A patent/TWI705055B/zh active
- 2016-04-28 DK DK16721748.8T patent/DK3288923T3/da active
- 2016-04-28 JP JP2017556167A patent/JP6691925B2/ja active Active
- 2016-04-28 BR BR112017022808-4A patent/BR112017022808B1/pt active IP Right Grant
- 2016-04-28 ES ES16721748T patent/ES2781780T3/es active Active
- 2016-04-28 EP EP16721748.8A patent/EP3288923B1/en 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 US US15/569,681 patent/US10125103B2/en active Active
- 2016-04-28 CN CN201680024155.6A patent/CN107531640B/zh active Active
- 2016-04-28 MX MX2017013632A patent/MX390887B/es unknown
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2017
- 2017-10-25 IL IL255256A patent/IL255256B/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031212A1 (de) * | 2005-09-17 | 2007-03-22 | Bayer Cropscience Ag | Verfahren zum herstellen von 5-fluor-1,3-dialkyl-1h-pyrazol-4-carbonsäurefluoriden |
| WO2010130767A2 (en) * | 2009-05-15 | 2010-11-18 | Bayer Cropscience Ag | Fungicide pyrazole carboxamides derivatives |
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| Publication number | Publication date |
|---|---|
| JP2018514538A (ja) | 2018-06-07 |
| JP6691925B2 (ja) | 2020-05-13 |
| US10125103B2 (en) | 2018-11-13 |
| US20180118690A1 (en) | 2018-05-03 |
| KR102585411B1 (ko) | 2023-10-05 |
| EP3288923B1 (en) | 2020-02-12 |
| MX2017013632A (es) | 2018-03-08 |
| WO2016174121A1 (en) | 2016-11-03 |
| BR112017022808B1 (pt) | 2022-04-19 |
| EP3288923A1 (en) | 2018-03-07 |
| CN107531640B (zh) | 2020-10-27 |
| IL255256A0 (en) | 2017-12-31 |
| DK3288923T3 (da) | 2020-04-20 |
| CN107531640A (zh) | 2018-01-02 |
| MX390887B (es) | 2025-03-21 |
| IL255256B (en) | 2020-05-31 |
| ES2781780T3 (es) | 2020-09-07 |
| BR112017022808A2 (pt) | 2018-07-17 |
| TW201704215A (zh) | 2017-02-01 |
| KR20170141764A (ko) | 2017-12-26 |
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