RU2346934C2 - Способ синтеза производных с гидрофторметиленсульфонильным радикалом - Google Patents
Способ синтеза производных с гидрофторметиленсульфонильным радикалом Download PDFInfo
- Publication number
- RU2346934C2 RU2346934C2 RU2005102101/04A RU2005102101A RU2346934C2 RU 2346934 C2 RU2346934 C2 RU 2346934C2 RU 2005102101/04 A RU2005102101/04 A RU 2005102101/04A RU 2005102101 A RU2005102101 A RU 2005102101A RU 2346934 C2 RU2346934 C2 RU 2346934C2
- Authority
- RU
- Russia
- Prior art keywords
- fluorine
- aforementioned
- amount
- water
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title description 15
- 238000003786 synthesis reaction Methods 0.000 title description 9
- 239000002904 solvent Substances 0.000 claims abstract description 28
- 239000008346 aqueous phase Substances 0.000 claims abstract description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 239000011737 fluorine Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 150000001721 carbon Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 5
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 5
- 238000009396 hybridization Methods 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 230000026030 halogenation Effects 0.000 claims abstract description 4
- 230000031709 bromination Effects 0.000 claims abstract description 3
- 238000005893 bromination reaction Methods 0.000 claims abstract description 3
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- -1 alkyl sulfide Chemical compound 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 16
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 11
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- CGDXUTMWWHKMOE-UHFFFAOYSA-N difluoromethanesulfonic acid Chemical class OS(=O)(=O)C(F)F CGDXUTMWWHKMOE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- PFTYKBCYTNZWCX-UHFFFAOYSA-N difluoromethanesulfinic acid Chemical compound OS(=O)C(F)F PFTYKBCYTNZWCX-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 150000003461 sulfonyl halides Chemical class 0.000 description 5
- PBKONEOXTCPAFI-UHFFFAOYSA-N TCB Natural products ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QMOWRNGLGDZHAF-UHFFFAOYSA-N difluoromethylsulfanylmethylbenzene Chemical compound FC(F)SCC1=CC=CC=C1 QMOWRNGLGDZHAF-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- JYQLKKNUGGVARY-UHFFFAOYSA-N difluoromethanesulfonyl chloride Chemical compound FC(F)S(Cl)(=O)=O JYQLKKNUGGVARY-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100369068 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) TDA1 gene Proteins 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogen, Water And Hydrids (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0208090 | 2002-06-28 | ||
| FR0208090A FR2841551B1 (fr) | 2002-06-28 | 2002-06-28 | Procede de synthese de derives a radical hydrogenofluoromethylene-sulfonyle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005102101A RU2005102101A (ru) | 2005-08-27 |
| RU2346934C2 true RU2346934C2 (ru) | 2009-02-20 |
Family
ID=29724975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005102101/04A RU2346934C2 (ru) | 2002-06-28 | 2003-06-24 | Способ синтеза производных с гидрофторметиленсульфонильным радикалом |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7534906B2 (https=) |
| EP (1) | EP1517888B1 (https=) |
| JP (1) | JP4531561B2 (https=) |
| CN (1) | CN100509776C (https=) |
| AT (1) | ATE395331T1 (https=) |
| AU (1) | AU2003260623A1 (https=) |
| CA (1) | CA2491207C (https=) |
| DE (1) | DE60320994D1 (https=) |
| FR (1) | FR2841551B1 (https=) |
| RU (1) | RU2346934C2 (https=) |
| WO (1) | WO2004002951A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2409559C1 (ru) * | 2009-08-03 | 2011-01-20 | Павел Анатольевич Семенов | Способ получения 1,1-дифторэтансульфохлорида |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101110602B (zh) * | 2006-07-20 | 2010-05-12 | 上海高清数字科技产业有限公司 | 基于多状态控制的载波捕获系统和方法 |
| RU2495878C2 (ru) | 2007-12-21 | 2013-10-20 | Ф.Хоффманн-Ля Рош Аг | Гетероциклические антивирусные соединения |
| CN110028390B (zh) * | 2019-05-28 | 2022-01-14 | 深圳大学 | 烷基二氟甲基醚类化合物的合成方法 |
| CN115594617B (zh) * | 2022-07-29 | 2024-02-06 | 苏州翔实医药发展有限公司 | 一种二氟甲基磺酰氯的合成方法 |
| CN116063208A (zh) * | 2023-02-13 | 2023-05-05 | 安徽省化工研究院 | 一种二氟甲烷磺酰氯的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2204545C2 (ru) * | 1995-03-24 | 2003-05-20 | Рон Пуленк Агрошими | Реактив и способ для введения замещенной дифторметильной группы в соединения, имеющие по меньшей мере одну электрофильную функцию |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2469401A1 (fr) * | 1979-11-13 | 1981-05-22 | Rhone Poulenc Ind | Procede de preparation de difluoromethane sulfonates alcalins |
| JPS5780366A (en) * | 1980-11-06 | 1982-05-19 | Sagami Chem Res Center | Bromodifluoromethyl sulfide and its preparation |
| JPS57146749A (en) * | 1981-01-29 | 1982-09-10 | Ici Ltd | Difluoromethane sulfonic acid and manufacture |
| FR2540108B1 (fr) * | 1983-02-02 | 1985-12-27 | Rhone Poulenc Spec Chim | Procede de preparation de perhalogenoalkylthioethers |
| FR2599366B1 (fr) * | 1986-05-28 | 1988-08-26 | Rhone Poulenc Spec Chim | Procede de preparation du sulfure de benzyle et de trifluoromethyle |
| EP0313939B1 (en) * | 1987-10-26 | 1992-09-16 | ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.) | Oxidation of thiols, disulfides and thiolsulfonates |
| DE3741309A1 (de) * | 1987-12-05 | 1989-06-15 | Bayer Ag | Verfahren zur herstellung von trifluormethansulfonsaeurechlorid |
| DE4333058A1 (de) * | 1993-09-29 | 1995-03-30 | Hoechst Ag | Verfahren zur Herstellung von Trifluorethylschwefelverbindungen aus Thiolaten und 1-Chlor-2,2,2-trifluorethan |
| JP3638357B2 (ja) * | 1994-11-01 | 2005-04-13 | 東洋化成工業株式会社 | ２，２−ジアルキル−３−アセトキシプロパンスルフォニルクロリドを製造する方法 |
| FR2730993B1 (fr) * | 1995-02-28 | 1997-04-04 | Rhone Poulenc Chimie | Procede de synthese de compose hydrocarbone fluore sur un carbone d'une chaine alcoyle |
| FR2743072B1 (fr) * | 1995-12-27 | 1998-02-27 | Electricite De France | Procede de preparation d'acides perfluoroalcanecarboxyliques et perfluoroalcanesulfoniques |
-
2002
- 2002-06-28 FR FR0208090A patent/FR2841551B1/fr not_active Expired - Fee Related
-
2003
- 2003-06-24 RU RU2005102101/04A patent/RU2346934C2/ru not_active IP Right Cessation
- 2003-06-24 AT AT03761633T patent/ATE395331T1/de not_active IP Right Cessation
- 2003-06-24 CN CNB038179326A patent/CN100509776C/zh not_active Expired - Lifetime
- 2003-06-24 AU AU2003260623A patent/AU2003260623A1/en not_active Abandoned
- 2003-06-24 JP JP2004516858A patent/JP4531561B2/ja not_active Expired - Lifetime
- 2003-06-24 DE DE60320994T patent/DE60320994D1/de not_active Expired - Lifetime
- 2003-06-24 WO PCT/FR2003/001940 patent/WO2004002951A2/fr not_active Ceased
- 2003-06-24 EP EP03761633A patent/EP1517888B1/fr not_active Expired - Lifetime
- 2003-06-24 US US10/519,287 patent/US7534906B2/en not_active Expired - Fee Related
- 2003-06-24 CA CA2491207A patent/CA2491207C/fr not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2204545C2 (ru) * | 1995-03-24 | 2003-05-20 | Рон Пуленк Агрошими | Реактив и способ для введения замещенной дифторметильной группы в соединения, имеющие по меньшей мере одну электрофильную функцию |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2409559C1 (ru) * | 2009-08-03 | 2011-01-20 | Павел Анатольевич Семенов | Способ получения 1,1-дифторэтансульфохлорида |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004002951A3 (fr) | 2004-04-15 |
| CA2491207C (fr) | 2012-02-21 |
| US7534906B2 (en) | 2009-05-19 |
| WO2004002951A2 (fr) | 2004-01-08 |
| EP1517888B1 (fr) | 2008-05-14 |
| CA2491207A1 (fr) | 2004-01-08 |
| FR2841551B1 (fr) | 2006-01-13 |
| JP4531561B2 (ja) | 2010-08-25 |
| US20060178536A1 (en) | 2006-08-10 |
| CN1671657A (zh) | 2005-09-21 |
| FR2841551A1 (fr) | 2004-01-02 |
| JP2005531626A (ja) | 2005-10-20 |
| CN100509776C (zh) | 2009-07-08 |
| EP1517888A2 (fr) | 2005-03-30 |
| RU2005102101A (ru) | 2005-08-27 |
| AU2003260623A1 (en) | 2004-01-19 |
| DE60320994D1 (de) | 2008-06-26 |
| ATE395331T1 (de) | 2008-05-15 |
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