DE69803186T2 - Katalysierte fluorierung von carbonylverbindungen - Google Patents
Katalysierte fluorierung von carbonylverbindungenInfo
- Publication number
- DE69803186T2 DE69803186T2 DE69803186T DE69803186T DE69803186T2 DE 69803186 T2 DE69803186 T2 DE 69803186T2 DE 69803186 T DE69803186 T DE 69803186T DE 69803186 T DE69803186 T DE 69803186T DE 69803186 T2 DE69803186 T2 DE 69803186T2
- Authority
- DE
- Germany
- Prior art keywords
- process according
- alkyl
- group
- compound
- cycloalkyl
- 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.)
- Expired - Fee Related
Links
- 150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 21
- 238000003682 fluorination reaction Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 29
- 239000011737 fluorine Substances 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 15
- 150000003623 transition metal compounds Chemical group 0.000 claims abstract description 13
- 150000003624 transition metals Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 230000003213 activating effect Effects 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- -1 fluorine-substituted carbon atom Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 239000012025 fluorinating agent Substances 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- BAQGNDVEQGZTOL-UHFFFAOYSA-N chloro 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCl BAQGNDVEQGZTOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 claims 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007858 starting material Substances 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 230000010354 integration Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920009441 perflouroethylene propylene Polymers 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- DHMGFEHFGCBYCM-UHFFFAOYSA-N C(C)NN(C(CC(=O)C)=O)NCC Chemical compound C(C)NN(C(CC(=O)C)=O)NCC DHMGFEHFGCBYCM-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- GOWQBFVDZPZZFA-UHFFFAOYSA-N diethyl 2-fluoropropanedioate Chemical compound CCOC(=O)C(F)C(=O)OCC GOWQBFVDZPZZFA-UHFFFAOYSA-N 0.000 description 2
- DAKKWKYIQGMKOS-UHFFFAOYSA-N diethyl 2-nitropropanedioate Chemical compound CCOC(=O)C([N+]([O-])=O)C(=O)OCC DAKKWKYIQGMKOS-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- GZJCDQYVIXPMAW-UHFFFAOYSA-N 1,2-dichloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1Cl GZJCDQYVIXPMAW-UHFFFAOYSA-N 0.000 description 1
- WMRXQMJJFZUNOZ-UHFFFAOYSA-N 1-fluoro-1-methylsulfonylpropan-2-one Chemical compound CC(=O)C(F)S(C)(=O)=O WMRXQMJJFZUNOZ-UHFFFAOYSA-N 0.000 description 1
- NWEYGXQKFVGUFR-UHFFFAOYSA-N 1-methylsulfonylpropan-2-one Chemical compound CC(=O)CS(C)(=O)=O NWEYGXQKFVGUFR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BDQNZEYYCYLVAC-UHFFFAOYSA-N 2,2-difluoro-4,4-dimethyl-3-oxopentanenitrile Chemical compound CC(C)(C)C(=O)C(F)(F)C#N BDQNZEYYCYLVAC-UHFFFAOYSA-N 0.000 description 1
- WSAJKOUEWHRILZ-UHFFFAOYSA-N 2-fluoro-4,4-dimethyl-3-oxopentanenitrile Chemical compound CC(C)(C)C(=O)C(F)C#N WSAJKOUEWHRILZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 1
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 101150113676 chr1 gene Proteins 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YTEKREICWGQLEN-UHFFFAOYSA-N diethyl 2-fluoro-2-nitropropanedioate Chemical compound CCOC(=O)C(F)([N+]([O-])=O)C(=O)OCC YTEKREICWGQLEN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005837 enolization reaction Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- UBBLSXAAOGZNJV-UHFFFAOYSA-N ethyl 2,2-difluoro-2-nitroacetate Chemical compound CCOC(=O)C(F)(F)[N+]([O-])=O UBBLSXAAOGZNJV-UHFFFAOYSA-N 0.000 description 1
- VSGIDAWRTVCNLF-UHFFFAOYSA-N ethyl 2-chloro-2-fluoro-3-oxobutanoate Chemical compound CCOC(=O)C(F)(Cl)C(C)=O VSGIDAWRTVCNLF-UHFFFAOYSA-N 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- UZLFSAIEQNZPEC-UHFFFAOYSA-N ethyl 2-cyano-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)C#N UZLFSAIEQNZPEC-UHFFFAOYSA-N 0.000 description 1
- PWHWKEZBNFYUED-UHFFFAOYSA-N ethyl 2-cyano-2-fluoroacetate Chemical compound CCOC(=O)C(F)C#N PWHWKEZBNFYUED-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- SLKHGQVZEQYSTP-UHFFFAOYSA-N ethyl 2-fluoro-2-nitroacetate Chemical compound CCOC(=O)C(F)[N+]([O-])=O SLKHGQVZEQYSTP-UHFFFAOYSA-N 0.000 description 1
- FTKASJMIPSSXBP-UHFFFAOYSA-N ethyl 2-nitroacetate Chemical compound CCOC(=O)C[N+]([O-])=O FTKASJMIPSSXBP-UHFFFAOYSA-N 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NAVBILUDFUBPHP-UHFFFAOYSA-N n,n-bis(ethylamino)-2-fluoro-3-oxobutanamide Chemical compound CCNN(NCC)C(=O)C(F)C(C)=O NAVBILUDFUBPHP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9715140A GB9715140D0 (en) | 1997-07-18 | 1997-07-18 | Fluorination of organic compounds |
| GB9715139A GB9715139D0 (en) | 1997-07-18 | 1997-07-18 | Fluorination of organic compounds |
| GBGB9808777.8A GB9808777D0 (en) | 1998-04-25 | 1998-04-25 | Fluorination of organic compounds |
| PCT/GB1998/001905 WO1999003802A1 (en) | 1997-07-18 | 1998-07-16 | Catalysed fluorination of carbonyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69803186D1 DE69803186D1 (de) | 2002-02-21 |
| DE69803186T2 true DE69803186T2 (de) | 2002-07-18 |
Family
ID=27268933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69803186T Expired - Fee Related DE69803186T2 (de) | 1997-07-18 | 1998-07-16 | Katalysierte fluorierung von carbonylverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6300511B1 (enExample) |
| EP (1) | EP0996606B1 (enExample) |
| JP (1) | JP2001510173A (enExample) |
| AT (1) | ATE212008T1 (enExample) |
| AU (1) | AU8346698A (enExample) |
| DE (1) | DE69803186T2 (enExample) |
| WO (1) | WO1999003802A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1454900A1 (en) * | 2003-03-07 | 2004-09-08 | Sanofi-Synthelabo | Process for the preparation of pyridinyl and pyrimidinyl mono-fluorinated beta keto-esters |
| WO2013028639A1 (en) * | 2011-08-19 | 2013-02-28 | The Trustees Of Princeton University | C-halogen bond formation |
| CN104418739A (zh) * | 2013-08-19 | 2015-03-18 | 上海元符医药科技有限公司 | 一种2-氟丙二酸二甲酯(i)的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4929317A (en) | 1986-12-01 | 1990-05-29 | Tokuyama Soda Kabushiki Kaisha | Process for preparation of perfluoro organic compounds |
| DE3827436A1 (de) * | 1988-08-12 | 1990-02-15 | Bayer Ag | Verfahren zum einfuehren von fluoratomen an aromatische kerne durch nucleophilen austausch |
| EP0781752B1 (en) | 1992-10-30 | 2001-02-21 | Daikin Industries, Limited | Process for preparing fluorine-containing dicarbonyl compound |
| WO1995014646A1 (en) * | 1993-11-20 | 1995-06-01 | Bnfl Fluorochemicals Ltd | The preparation of dicarbonyls |
-
1998
- 1998-07-16 AU AU83466/98A patent/AU8346698A/en not_active Abandoned
- 1998-07-16 EP EP98933760A patent/EP0996606B1/en not_active Expired - Lifetime
- 1998-07-16 US US09/463,030 patent/US6300511B1/en not_active Expired - Fee Related
- 1998-07-16 WO PCT/GB1998/001905 patent/WO1999003802A1/en not_active Ceased
- 1998-07-16 DE DE69803186T patent/DE69803186T2/de not_active Expired - Fee Related
- 1998-07-16 AT AT98933760T patent/ATE212008T1/de not_active IP Right Cessation
- 1998-07-16 JP JP2000503036A patent/JP2001510173A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU8346698A (en) | 1999-02-10 |
| US6300511B1 (en) | 2001-10-09 |
| EP0996606A1 (en) | 2000-05-03 |
| EP0996606B1 (en) | 2002-01-16 |
| ATE212008T1 (de) | 2002-02-15 |
| JP2001510173A (ja) | 2001-07-31 |
| DE69803186D1 (de) | 2002-02-21 |
| WO1999003802A1 (en) | 1999-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3125662A1 (de) | Verfahren und katalysator zur herstellung von cyclischen iminen | |
| DE2924133C2 (enExample) | ||
| DE2624891A1 (de) | Verfahren zur herstellung von benzoylcyanid | |
| DE2454950C2 (de) | Verfahren zur Herstellung von 2-Aminobutan-1-ol und von dessen Säureanlagerungssalzen | |
| DE68904731T2 (de) | O-hydroxyalkylierung von 1,1-dihydro-perfluorierten alkoholen. | |
| DE2614241C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2756560C2 (de) | Verfahren zur Herstellung von Piperonal | |
| DE2323867A1 (de) | Verfahren zur herstellung ungesaettigter aldehydcyanhydrine | |
| DE2443142C2 (de) | Verfahren zur Herstellung von Cyclopropancarbonsäurenitril | |
| DE1618207B2 (de) | Verfahren zur herstellung von alphachloracetessigsaeure-monoalkylamiden | |
| DE69230358T2 (de) | Substituiertes N-Fluoropyridiniumsulfonat, Zwischenprodukte und Verfahren zur Herstellung davon | |
| DE60010092T2 (de) | Verfahren zur herstellung von acylierten 1,3-dicarbonylverbindungen | |
| DE3029368C2 (enExample) | ||
| DE3029134C2 (de) | Verfahren zur Herstellung von halogenierten aliphatischen Ethern | |
| DE68904350T2 (de) | Herstellung von 3,5,6-trichlorpyridin-2-ol und zwischenprodukte dafuer. | |
| DE3509911C2 (de) | Verfahren zur Herstellung von Trifluoressigsäure aus Trichlortrifluorethan | |
| DE69713098T2 (de) | Verfahren zur monoacylierung von hydroxytaxanen | |
| DE2717075A1 (de) | Verfahren zur herstellung von benzoylcyanid | |
| US6300511B1 (en) | Catalyzed fluorination of carbonyl compounds | |
| DE69115389T2 (de) | Cyclohexenol Derivate | |
| DE2720911C3 (de) | Verfahren zur Herstellung von n-Hexyl-Carboran | |
| DE69837852T2 (de) | Derivate von o-(perfluor)dibenzofuranium-salzen, zwischenprodukte zu ihrer herstellung, verfahren zur herstellung der zwischenprodukte, perfluoralkylierungsmittel und perfluoralkylierungsverfahren | |
| DE69918169T2 (de) | Verfahren zur herstellung von aromatischen thioethern vom diphenyltyp | |
| DE19853863C1 (de) | Verfahren zur Herstellung von Oxadiazolonen | |
| DE2259791A1 (de) | Verfahren zur herstellung von thionamiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |