NO311254B1 - Fremgangsmåte for fremstilling av cyanobifenyl - Google Patents
Fremgangsmåte for fremstilling av cyanobifenyl Download PDFInfo
- Publication number
- NO311254B1 NO311254B1 NO19991118A NO991118A NO311254B1 NO 311254 B1 NO311254 B1 NO 311254B1 NO 19991118 A NO19991118 A NO 19991118A NO 991118 A NO991118 A NO 991118A NO 311254 B1 NO311254 B1 NO 311254B1
- Authority
- NO
- Norway
- Prior art keywords
- salt
- palladium
- catalyst
- solvent
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 230000008569 process Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 6
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 title description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 239000003426 co-catalyst Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 13
- -1 p-tolylmagnesium halide Chemical class 0.000 claims description 11
- 150000002940 palladium Chemical class 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- ZGQVZLSNEBEHFN-UHFFFAOYSA-N 2-(4-methylphenyl)benzonitrile Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C#N ZGQVZLSNEBEHFN-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 150000002696 manganese Chemical class 0.000 claims description 7
- 150000002815 nickel Chemical class 0.000 claims description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- AFMPMSCZPVNPEM-UHFFFAOYSA-N 2-bromobenzonitrile Chemical group BrC1=CC=CC=C1C#N AFMPMSCZPVNPEM-UHFFFAOYSA-N 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical group [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims description 2
- 150000003057 platinum Chemical class 0.000 claims description 2
- 238000001354 calcination Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001868 cobalt Chemical class 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 11
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910002666 PdCl2 Inorganic materials 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- YBPFQOFSPMWGKA-UHFFFAOYSA-M [Cl-].CC1=CC=C([Mg+])C=C1 Chemical compound [Cl-].CC1=CC=C([Mg+])C=C1 YBPFQOFSPMWGKA-UHFFFAOYSA-M 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- KHTFVXZBUYUMCT-UHFFFAOYSA-N 5,5-dimethyl-2-phenylcyclohexa-1,3-diene Chemical group C1=CC(C)(C)CC=C1C1=CC=CC=C1 KHTFVXZBUYUMCT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- BVUQKCCKUOSAEV-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1 BVUQKCCKUOSAEV-UHFFFAOYSA-M 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 235000002867 manganese chloride Nutrition 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CKDXMVPILZEZSP-UHFFFAOYSA-N 2-(2-methylphenyl)benzonitrile Chemical compound CC1=CC=CC=C1C1=CC=CC=C1C#N CKDXMVPILZEZSP-UHFFFAOYSA-N 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical class [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9610970A FR2753195B1 (fr) | 1996-09-09 | 1996-09-09 | Procede pour la preparation d'un cyanobiphenyle |
| PCT/FR1997/001577 WO1998009941A1 (fr) | 1996-09-09 | 1997-09-08 | Procede pour la preparation d'un cyanobiphenyle |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991118L NO991118L (no) | 1999-03-08 |
| NO991118D0 NO991118D0 (no) | 1999-03-08 |
| NO311254B1 true NO311254B1 (no) | 2001-11-05 |
Family
ID=9495567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991118A NO311254B1 (no) | 1996-09-09 | 1999-03-08 | Fremgangsmåte for fremstilling av cyanobifenyl |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6392080B1 (de) |
| EP (1) | EP0931059B1 (de) |
| JP (1) | JP3264497B2 (de) |
| AT (1) | ATE210633T1 (de) |
| AU (1) | AU4211797A (de) |
| BR (1) | BR9711953A (de) |
| CA (1) | CA2265438C (de) |
| DE (1) | DE69709143T2 (de) |
| FR (1) | FR2753195B1 (de) |
| NO (1) | NO311254B1 (de) |
| WO (1) | WO1998009941A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7501448B2 (en) * | 2004-10-15 | 2009-03-10 | Teva Pharmaceutical Industries, Ltd. | Process for preparing telmisartan |
| EP2233459A4 (de) * | 2007-12-21 | 2011-04-27 | Sumitomo Chemical Co | VERFAHREN ZUR HERSTELLUNG EINER konjugierten AROMATISCHEN VERBINDUNG |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1334092C (en) | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| DE3816120A1 (de) * | 1988-05-11 | 1989-11-23 | Bayer Ag | Verfahren zur herstellung von unsymmetrischen biarylverbindungen |
| GB9017480D0 (en) * | 1990-08-09 | 1990-09-26 | Ici Plc | Chemical process |
| FR2689887B1 (fr) * | 1992-04-13 | 1995-06-23 | Sanofi Elf | Procede de preparation d'un derive de biphenyle. |
| US5380910A (en) * | 1992-04-28 | 1995-01-10 | Ihara Chemical Industry Co., Ltd. | Method for producing an asymmetric biaryl derivative |
-
1996
- 1996-09-09 FR FR9610970A patent/FR2753195B1/fr not_active Expired - Fee Related
-
1997
- 1997-09-08 AU AU42117/97A patent/AU4211797A/en not_active Abandoned
- 1997-09-08 CA CA002265438A patent/CA2265438C/fr not_active Expired - Fee Related
- 1997-09-08 JP JP51231898A patent/JP3264497B2/ja not_active Expired - Fee Related
- 1997-09-08 WO PCT/FR1997/001577 patent/WO1998009941A1/fr active IP Right Grant
- 1997-09-08 BR BR9711953A patent/BR9711953A/pt not_active IP Right Cessation
- 1997-09-08 AT AT97940192T patent/ATE210633T1/de not_active IP Right Cessation
- 1997-09-08 EP EP97940192A patent/EP0931059B1/de not_active Expired - Lifetime
- 1997-09-08 US US09/147,787 patent/US6392080B1/en not_active Expired - Lifetime
- 1997-09-08 DE DE69709143T patent/DE69709143T2/de not_active Expired - Lifetime
-
1999
- 1999-03-08 NO NO19991118A patent/NO311254B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000501427A (ja) | 2000-02-08 |
| AU4211797A (en) | 1998-03-26 |
| WO1998009941A1 (fr) | 1998-03-12 |
| US6392080B1 (en) | 2002-05-21 |
| NO991118L (no) | 1999-03-08 |
| CA2265438C (fr) | 2003-07-08 |
| BR9711953A (pt) | 1999-08-24 |
| ATE210633T1 (de) | 2001-12-15 |
| EP0931059A1 (de) | 1999-07-28 |
| FR2753195A1 (fr) | 1998-03-13 |
| EP0931059B1 (de) | 2001-12-12 |
| CA2265438A1 (fr) | 1998-03-12 |
| NO991118D0 (no) | 1999-03-08 |
| JP3264497B2 (ja) | 2002-03-11 |
| FR2753195B1 (fr) | 1998-11-27 |
| DE69709143T2 (de) | 2002-08-01 |
| DE69709143D1 (de) | 2002-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO311254B1 (no) | Fremgangsmåte for fremstilling av cyanobifenyl | |
| EP2298756A1 (de) | Verfahren zur herstellung von 3-methyl-2-thiophencarbonsäure | |
| US20030149272A1 (en) | Method for preparing a polyaromatic compound | |
| IL46917A (en) | Preparation of 2-nitrobenzaldehyde and 2-nitrobenzylidenechloride | |
| JP2000169425A (ja) | ２―アルキル―３―ヒドロキシ安息香酸の製造方法 | |
| CN113511970B (zh) | 一种芳基取代的炔烃的合成方法 | |
| US20010034459A1 (en) | Process for preparing 4'-trifluoromethyl-2-methylbiphenyl and 4'-trifluoromethyl-biphenyl-2-carboxylic acid from o-tolylmetallates | |
| RU2243207C2 (ru) | Способы получения промежуточных продуктов для синтеза пестицидов | |
| NO326192B1 (no) | Fremgangsmate for fremstilling av 4-metyl-bifenyl-derivater | |
| JPS6116376B2 (de) | ||
| Gillespie et al. | Rhodium (II)-catalysed addition of dimethyl diazomalonate to thiophen: a simple synthesis of thiophenium bismethoxycarbonylmethylides and crystal and molecular structure of the unsubstituted methylide | |
| KR100332160B1 (ko) | 시클로알킬및할로알킬o-아미노페닐케톤의개선된제조방법 | |
| MXPA99002145A (en) | Method for preparing a cyanobiphenyl | |
| US5336653A (en) | Catalyst for asymmetric synthesis | |
| JP2000095730A (ja) | ハロゲン化フェニルマロン酸エステルの製造方法 | |
| KR20080067346A (ko) | 비페닐의 제조방법 | |
| JP2960183B2 (ja) | 新規なテルペン誘導体及びその製造方法 | |
| WO1993001173A1 (en) | Production of aromatic olefins | |
| US6392051B2 (en) | Process for preparing 4-(4′-carboxyphenyl)pyridine | |
| JP2797211B2 (ja) | ベンゾ―１，３―ジオキソールの製造方法 | |
| US6197964B1 (en) | Method for the production of 2,6-dichloro-5-fluoronicotinonitrile and the chemical compound 3-cyano-2-hydroxy-5-fluoropyride-6-one-monosodium salt its tautomers | |
| JP3505991B2 (ja) | ４，５−ジ置換アントラニルアミドの製造法 | |
| KR910003635B1 (ko) | 2-(2-나프틸옥시)프로피온아닐리드 유도체의 제조방법 | |
| JP2727104B2 (ja) | ジアリール誘導体の製造方法 | |
| SU963462A3 (ru) | Способ получени 2-арилпропионовой кислоты |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |