FR2471974A1 - Procede de preparation de fluorures de fluorobenzene sulfonyle - Google Patents
Procede de preparation de fluorures de fluorobenzene sulfonyle Download PDFInfo
- Publication number
- FR2471974A1 FR2471974A1 FR7931220A FR7931220A FR2471974A1 FR 2471974 A1 FR2471974 A1 FR 2471974A1 FR 7931220 A FR7931220 A FR 7931220A FR 7931220 A FR7931220 A FR 7931220A FR 2471974 A1 FR2471974 A1 FR 2471974A1
- Authority
- FR
- France
- Prior art keywords
- formula
- equal
- fluoride
- radical
- solvent
- 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
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 239000002798 polar solvent Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 26
- -1 alkyl radical Chemical class 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 16
- 239000003352 sequestering agent Substances 0.000 claims description 14
- 239000007983 Tris buffer Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 abstract description 3
- UOECQWWSUHZUMI-UHFFFAOYSA-N 2-chlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC=CC=C1Cl UOECQWWSUHZUMI-UHFFFAOYSA-N 0.000 abstract 1
- ODVXTZVBPYPQLJ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl fluoride Chemical class FC1=CC=CC=C1S(F)(=O)=O ODVXTZVBPYPQLJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 8
- 239000011698 potassium fluoride Substances 0.000 description 6
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- AZLGIYPCGAIVBH-UHFFFAOYSA-N chlorobenzene;sulfuryl difluoride Chemical compound FS(F)(=O)=O.ClC1=CC=CC=C1 AZLGIYPCGAIVBH-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 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 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- TXWKSFNVNFDKQQ-UHFFFAOYSA-N fluorobenzene;sulfuryl difluoride Chemical class FS(F)(=O)=O.FC1=CC=CC=C1 TXWKSFNVNFDKQQ-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WNVVRCKTQSCPAC-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1Cl WNVVRCKTQSCPAC-UHFFFAOYSA-N 0.000 description 2
- OJWNNJCWEKRYRU-UHFFFAOYSA-N 2,4-difluorobenzenesulfonyl fluoride Chemical compound FC1=CC=C(S(F)(=O)=O)C(F)=C1 OJWNNJCWEKRYRU-UHFFFAOYSA-N 0.000 description 2
- AMJKUTUQZZVWMJ-UHFFFAOYSA-N 4-fluorobenzenesulfonyl fluoride Chemical compound FC1=CC=C(S(F)(=O)=O)C=C1 AMJKUTUQZZVWMJ-UHFFFAOYSA-N 0.000 description 2
- IZTXDEZRLVGMPY-UHFFFAOYSA-N 5-chloro-2,4-difluorobenzenesulfonyl fluoride Chemical compound FC1=CC(F)=C(S(F)(=O)=O)C=C1Cl IZTXDEZRLVGMPY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- SGSPZQWCFIJLHS-UHFFFAOYSA-N S(=O)(=O)(F)F.FC=1C=CC=C(C1)F Chemical compound S(=O)(=O)(F)F.FC=1C=CC=C(C1)F SGSPZQWCFIJLHS-UHFFFAOYSA-N 0.000 description 2
- 229910006095 SO2F Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VBNBTXAHDDGMNR-UHFFFAOYSA-N 1,3-dichlorobenzene;sulfuryl difluoride Chemical compound FS(F)(=O)=O.ClC1=CC=CC(Cl)=C1 VBNBTXAHDDGMNR-UHFFFAOYSA-N 0.000 description 1
- LYDBMJRBEFPWSM-UHFFFAOYSA-N 1-chloro-2-fluorobenzene;sulfuryl difluoride Chemical compound FS(F)(=O)=O.FC1=CC=CC=C1Cl LYDBMJRBEFPWSM-UHFFFAOYSA-N 0.000 description 1
- FVLXVAQJAAJFSA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl FVLXVAQJAAJFSA-UHFFFAOYSA-N 0.000 description 1
- PUYJBWSFLASCBC-UHFFFAOYSA-N 2,4,6-trifluorobenzenesulfonyl fluoride Chemical compound FC1=CC(F)=C(S(F)(=O)=O)C(F)=C1 PUYJBWSFLASCBC-UHFFFAOYSA-N 0.000 description 1
- FDTPBIKNYWQLAE-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FDTPBIKNYWQLAE-UHFFFAOYSA-N 0.000 description 1
- RULYNRDLKTTWGC-UHFFFAOYSA-N 2-(2-butoxyethoxy)-n,n-bis[2-(2-butoxyethoxy)ethyl]ethanamine Chemical compound CCCCOCCOCCN(CCOCCOCCCC)CCOCCOCCCC RULYNRDLKTTWGC-UHFFFAOYSA-N 0.000 description 1
- XZGIHWAIIZHXKX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-n,n-bis[2-(2-ethoxyethoxy)ethyl]ethanamine Chemical compound CCOCCOCCN(CCOCCOCC)CCOCCOCC XZGIHWAIIZHXKX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JIFAWAXKXDTUHW-UHFFFAOYSA-N 2-fluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1F JIFAWAXKXDTUHW-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- OIATXTBHBNSAHQ-UHFFFAOYSA-N 3,5-dichloro-2,6-difluorobenzenesulfonyl fluoride Chemical compound FC1=C(Cl)C=C(Cl)C(F)=C1S(F)(=O)=O OIATXTBHBNSAHQ-UHFFFAOYSA-N 0.000 description 1
- OGXDGSIBAVAFPS-UHFFFAOYSA-N 3-chloro-2,4,6-trifluorobenzenesulfonyl fluoride Chemical compound FC1=CC(F)=C(S(F)(=O)=O)C(F)=C1Cl OGXDGSIBAVAFPS-UHFFFAOYSA-N 0.000 description 1
- NVXAPNQXZMRRLE-UHFFFAOYSA-N 3-chloro-2,4-difluorobenzenesulfonyl fluoride Chemical compound FC1=CC=C(S(F)(=O)=O)C(F)=C1Cl NVXAPNQXZMRRLE-UHFFFAOYSA-N 0.000 description 1
- PCTLRVPDZBVCMP-UHFFFAOYSA-N 4-chlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC=C(Cl)C=C1 PCTLRVPDZBVCMP-UHFFFAOYSA-N 0.000 description 1
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PWTZGWCQOYHSAL-UHFFFAOYSA-N ClC1=CC(Cl)=CC=C1.F Chemical compound ClC1=CC(Cl)=CC=C1.F PWTZGWCQOYHSAL-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WGAWQOVXRFAOHS-UHFFFAOYSA-N F.Cl.Cl.Cl.Cl Chemical compound F.Cl.Cl.Cl.Cl WGAWQOVXRFAOHS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- QAVLBKLSFDPJOG-UHFFFAOYSA-N S(=O)(=O)(F)F.ClC=1C(=C(C(=C(C1)Cl)Cl)Cl)Cl Chemical compound S(=O)(=O)(F)F.ClC=1C(=C(C(=C(C1)Cl)Cl)Cl)Cl QAVLBKLSFDPJOG-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- ZMCOWIJJSXOLAZ-UHFFFAOYSA-N chlorobenzene;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.ClC1=CC=CC=C1 ZMCOWIJJSXOLAZ-UHFFFAOYSA-N 0.000 description 1
- 101150113676 chr1 gene Proteins 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FIIZQHKGJMRJIL-UHFFFAOYSA-N n,3-diphenylprop-2-enamide Chemical compound C=1C=CC=CC=1C=CC(=O)NC1=CC=CC=C1 FIIZQHKGJMRJIL-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QXGDIAJDPHVEBJ-UHFFFAOYSA-N sodium;heptan-1-olate Chemical compound [Na+].CCCCCCC[O-] QXGDIAJDPHVEBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- DVQMPCUEJVZIHX-UHFFFAOYSA-N sulfuryl dichloride;1,2,3-trichlorobenzene Chemical compound ClS(Cl)(=O)=O.ClC1=CC=CC(Cl)=C1Cl DVQMPCUEJVZIHX-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7931220A FR2471974A1 (fr) | 1979-12-20 | 1979-12-20 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
| DE8080401752T DE3063919D1 (en) | 1979-12-20 | 1980-12-08 | Process for preparing fluorobenzene-sulfonyl fluorides |
| EP80401752A EP0032077B1 (fr) | 1979-12-20 | 1980-12-08 | Procédé de préparation de fluorures de fluorobenzène sulfonyle |
| AT80401752T ATE3856T1 (de) | 1979-12-20 | 1980-12-08 | Verfahren zur herstellung fluorobenzen-sulfonyl- fluoriden. |
| US06/216,914 US4369145A (en) | 1979-12-20 | 1980-12-16 | Preparation of fluorobenzenesulfonyl fluorides by exchange fluorination |
| JP17812780A JPS56127350A (en) | 1979-12-20 | 1980-12-18 | Manufacture of fluorinated fluorobenzenesulfonyl |
| CA000367253A CA1153388A (fr) | 1979-12-20 | 1980-12-19 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7931220A FR2471974A1 (fr) | 1979-12-20 | 1979-12-20 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2471974A1 true FR2471974A1 (fr) | 1981-06-26 |
| FR2471974B1 FR2471974B1 (cg-RX-API-DMAC7.html) | 1984-02-24 |
Family
ID=9232996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7931220A Granted FR2471974A1 (fr) | 1979-12-20 | 1979-12-20 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4369145A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0032077B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56127350A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE3856T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1153388A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3063919D1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2471974A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063872B1 (en) * | 1981-04-27 | 1985-07-17 | Imperial Chemical Industries Plc | Process for the preparation of fluoromethyl pyridines and certain novel products obtained therefrom |
| US4886629A (en) * | 1988-06-06 | 1989-12-12 | Allied-Signal Inc. | Process for the preparation of fluorinated benzene sulfonyl fluorides |
| US4937397A (en) * | 1988-11-28 | 1990-06-26 | The Dow Chemical Company | Preparation of halofluorobenzenes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1360917A (fr) * | 1962-05-11 | 1964-05-15 | Nat Smelting Co Ltd | Procédé de fluoruration de composés perhalogénés et produits obtenus |
| FR1446914A (fr) * | 1964-09-16 | 1966-07-22 | Imp Smelting Corp Ltd | Procédé de préparation de nouveaux fluorures d'aryl-sulfonyle |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL302228A (cg-RX-API-DMAC7.html) * | 1962-12-20 | |||
| GB1004375A (en) * | 1963-10-03 | 1965-09-15 | Ici Ltd | Process for making fluorochlorobenzenes and hexafluorobenzene |
| GB1052462A (cg-RX-API-DMAC7.html) * | 1964-09-16 |
-
1979
- 1979-12-20 FR FR7931220A patent/FR2471974A1/fr active Granted
-
1980
- 1980-12-08 AT AT80401752T patent/ATE3856T1/de not_active IP Right Cessation
- 1980-12-08 DE DE8080401752T patent/DE3063919D1/de not_active Expired
- 1980-12-08 EP EP80401752A patent/EP0032077B1/fr not_active Expired
- 1980-12-16 US US06/216,914 patent/US4369145A/en not_active Expired - Fee Related
- 1980-12-18 JP JP17812780A patent/JPS56127350A/ja active Granted
- 1980-12-19 CA CA000367253A patent/CA1153388A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1360917A (fr) * | 1962-05-11 | 1964-05-15 | Nat Smelting Co Ltd | Procédé de fluoruration de composés perhalogénés et produits obtenus |
| FR1446914A (fr) * | 1964-09-16 | 1966-07-22 | Imp Smelting Corp Ltd | Procédé de préparation de nouveaux fluorures d'aryl-sulfonyle |
Non-Patent Citations (3)
| Title |
|---|
| CA1965 * |
| CA1967 * |
| EXBK/66 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0032077B1 (fr) | 1983-06-22 |
| CA1153388A (fr) | 1983-09-06 |
| FR2471974B1 (cg-RX-API-DMAC7.html) | 1984-02-24 |
| US4369145A (en) | 1983-01-18 |
| EP0032077A1 (fr) | 1981-07-15 |
| JPS5741465B2 (cg-RX-API-DMAC7.html) | 1982-09-03 |
| ATE3856T1 (de) | 1983-07-15 |
| JPS56127350A (en) | 1981-10-06 |
| DE3063919D1 (en) | 1983-07-28 |
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