WO1994008931A1 - Process and intermediates for the preparation of substituted 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentanes - Google Patents
Process and intermediates for the preparation of substituted 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentanes Download PDFInfo
- Publication number
- WO1994008931A1 WO1994008931A1 PCT/EP1993/002843 EP9302843W WO9408931A1 WO 1994008931 A1 WO1994008931 A1 WO 1994008931A1 EP 9302843 W EP9302843 W EP 9302843W WO 9408931 A1 WO9408931 A1 WO 9408931A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- suitable solvent
- preparation
- reacted
- meanings given
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000000543 intermediate Substances 0.000 title claims abstract description 7
- BWCCUAGATLHHOL-UHFFFAOYSA-N 1-phenoxy-3-(5,5,5-trifluoro-4-phenylpentyl)benzene Chemical class C=1C=CC=CC=1C(C(F)(F)F)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 BWCCUAGATLHHOL-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000460 chlorine Chemical group 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 methoxy, difluoromethoxy, ethoxy Chemical group 0.000 claims abstract description 6
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000001361 allenes Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 claims description 3
- KIMSDLZUYPIAMV-UHFFFAOYSA-N 3-phenoxy-3-phenylprop-1-yn-1-ol Chemical compound C=1C=CC=CC=1C(C#CO)OC1=CC=CC=C1 KIMSDLZUYPIAMV-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GBFUISVVTYNAKO-UHFFFAOYSA-N 1-(3-phenoxyphenyl)prop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GBFUISVVTYNAKO-UHFFFAOYSA-N 0.000 description 1
- YRWMHYYIDVURHR-UHFFFAOYSA-N 1-(4-fluoro-3-phenoxyphenyl)prop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 YRWMHYYIDVURHR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 1
- LPXPZLUYPHDYTH-UHFFFAOYSA-N 4-(4-ethoxyphenyl)-5,5,5-trifluoro-1-(4-fluoro-3-phenoxyphenyl)pent-2-yne-1,4-diol Chemical compound C1=CC(OCC)=CC=C1C(O)(C(F)(F)F)C#CC(O)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 LPXPZLUYPHDYTH-UHFFFAOYSA-N 0.000 description 1
- HRIQKBZGXPQASK-UHFFFAOYSA-N 4-[1,2-dichloro-4-(4-ethoxyphenyl)-5,5,5-trifluoropenta-2,3-dienyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)=C=C(Cl)C(Cl)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HRIQKBZGXPQASK-UHFFFAOYSA-N 0.000 description 1
- ZDKOCUQZTCGTSU-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-5,5,5-trifluoropentyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 ZDKOCUQZTCGTSU-UHFFFAOYSA-N 0.000 description 1
- JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- OWSNXLPHOKXBBX-UHFFFAOYSA-N Nc(cc1Nc2ccccc2)ccc1N Chemical compound Nc(cc1Nc2ccccc2)ccc1N OWSNXLPHOKXBBX-UHFFFAOYSA-N 0.000 description 1
- AGYCTGMCEHWULW-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C=C(C=CC=1)CC=C=CC(F)(F)F Chemical compound O(C1=CC=CC=C1)C=1C=C(C=CC=1)CC=C=CC(F)(F)F AGYCTGMCEHWULW-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- RFUGMORVSDZBLC-UHFFFAOYSA-N [Na].CC(N)=O Chemical compound [Na].CC(N)=O RFUGMORVSDZBLC-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FWLKYEAOOIPJRL-UHFFFAOYSA-N prop-1-yn-1-ol Chemical compound CC#CO FWLKYEAOOIPJRL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
Definitions
- This invention relates to a new process and new intermediates for the preparation of substituted 2-phenyl- 5-(3-phenoxyphenyl) -1, 1,l-trifluoropentanes of general formula I
- R l is fluorine, chlorine, methoxy, difluoromethoxy, ethoxy or trifluoroethoxy
- R 2 and R 3 independently of each other, are hydrogen or fluorine.
- the preparations described in this document have the disadvantage that they comprise many reaction stages.
- a further disadvantage is that one of the reaction stages comprises a Wittig reaction in which a large amount of triphenylphosphine oxide is formed as by-product.
- W is hydrogen or halogen
- X is hydrogen or fluorine
- Q is a group -(CF 2 ) n R 1 , in which R 1 is hydrogen, fluorine or chlorine and n is 1 or 2, and Z is halogen, C 1 -c 6 -alkyl, c 1 -C 6 -alkoxy, halo-C [ -c 6 -alkyl or halo- C 1 -C 6 -al oxy.
- This process also proceeds via a ittig reaction.
- the object of the invention is thus to provide a process with a smaller number of steps and which also avoids the Wittig reaction.
- R 3 has the meaning given in formula I
- acetylene in which R 3 has the meaning given in formula I, is reacted with acetylene in a suitable solvent with a strong base, in which the acetylene is deprotonated before the reaction,
- R 1 , R 2 and R 3 have the meaning given in general formula I is reacted with the halogenating agent in a suitable solvent, optionally using a base and finally
- R 1 , R 2 and R 3 have the meaning given in general formula I and Hal is chlorine or bromine is catalytically hydrogenated in a suitable solvent, optionally with the addition of an acid binding agent, or
- R 1 and R 2 have the meanings given in general formula I, is reacted with acetylene and a strong base or with sodium acetylide in a suitable solvent.
- the reaction step a) is suitably carried at a temperature of between -78°C at room temperature, in which as the base, there can be used for example sodium amide, sodium hydride or a Grignard reagent and as the solvent there can be used for example an ether, such as diethyl ether, a hydrocarbon, such as toluene, or liquid ammonia.
- the base there can be used for example sodium amide, sodium hydride or a Grignard reagent
- the solvent there can be used for example an ether, such as diethyl ether, a hydrocarbon, such as toluene, or liquid ammonia.
- phase transfer catalysed ethynylation is also possible, using concentrated alkali metal hydroxide as a base.
- the reaction step b) is suitably carried out at a temperature of between -78 ⁇ C and 0°C, in which as the base, there can be used for example n-butyllithium and as the solvent, there can be used for example an ether, such as diethyl ether or tetrahydrofuran, or a hydrocarbon, such as hexane or toluene.
- the base there can be used for example n-butyllithium
- the solvent there can be used for example an ether, such as diethyl ether or tetrahydrofuran, or a hydrocarbon, such as hexane or toluene.
- the reaction stage c) is suitably carried out at a temperature between 0 ⁇ C and 120°C in which there can be used, as halogenating agent for example thionyl chloride, phosphorus tribromide or concentrated hydrobromic acid, as the base for example pyridine or imidazole and as the solvent for example a hydrocarbon, such as toluene, a halogenated hydrocarbon, such as chloroform or dichloromethane, an ether, such as diethyl ether or tetrahydrofuran, a nitr x.e , such as acetonitrile, or an amide, such as dimethylforma ide.
- This reaction step can also be carried out without a solvent.
- Reaction step d) is suitably carried out at a temperature between room temperature and 200°C, under a hydrogen partial pressure of 1-150 bar.
- catalyst for the catalytic hydrogenation there is preferably used palladium on active charcoal.
- solvents it is preferable to use an alcohol, such as methanol or ethanol, or acetic acid.
- acid binding agent sodium acetate is preferred.
- the reaction step e) is suitably carried out at a temperature between -78°C and room temperature.
- Suitable bases are for example Grignard reagents.
- solvent there can be used ethers, such as diethyl ether or hydrocarbons, such as toluene or xylene.
- Reaction step f) is suitably carried out at a temperature between -78 ⁇ C and room temperature.
- Suitable bases include for example n-butyllithium, Grignard reagents, sodium hydride or sodium amide.
- Suitable solvents include for example ethers, such as diethyl ether, hydrocarbons such as toluene or hexane, nitriles such as acetonitrile, or liquid ammonia.
- the invention also includes diols of general formula V
- reaction steps a)-c) can be combined.
- the aldehyde of general formula II can be reacted with sodium acetamide in tetrahydrofuran. Without working up, an equivalent of n-butyllithium and then the ketone general formula I can be added. Then this can be worked up with water to the diol of general formula II or can be further converted with a halogenating agent directly into the allene of general formula VI, in which optionally acetonitrile or di ethylformamide can be added.
- a reaction sequence can also begin with a ketone of general formula IV in which, after the addition of butyllithium, the aldehyde of general formula II is added.
- the compounds of general formula I have one chiral centre, whereas the compounds of general formula V and VI have two.
- the invention includes all enantiomers and diastereoisomers, as well as their mixtures.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU51778/93A AU5177893A (en) | 1992-10-15 | 1993-10-14 | Process and intermediates for the preparation of substituted 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentanes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4235228 | 1992-10-15 | ||
| DEP4235228.2 | 1992-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994008931A1 true WO1994008931A1 (en) | 1994-04-28 |
Family
ID=6470812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1993/002843 WO1994008931A1 (en) | 1992-10-15 | 1993-10-14 | Process and intermediates for the preparation of substituted 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentanes |
Country Status (7)
| Country | Link |
|---|---|
| CN (1) | CN1090838A (enrdf_load_stackoverflow) |
| AU (1) | AU5177893A (enrdf_load_stackoverflow) |
| IL (1) | IL107161A0 (enrdf_load_stackoverflow) |
| MX (1) | MX9306388A (enrdf_load_stackoverflow) |
| TW (1) | TW247903B (enrdf_load_stackoverflow) |
| WO (1) | WO1994008931A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA937677B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133279A (en) * | 1996-06-26 | 2000-10-17 | Chugai Seiyaku Kabushiki Kaisha | Therapeutic agents for renal diseases and organ preservatives |
| WO2012150206A2 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Neue cyclopropansäureeesterderivate als schädlingsbekämpfungsmittel |
| WO2012150207A1 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Verwendung von cyclopropancarbonsäureeesterderivaten zur bekämpfung von insektizid-resistenten insekten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115819662B (zh) * | 2022-12-18 | 2023-09-12 | 四川轻化工大学 | 一种含氟环氧树脂及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233834A1 (en) * | 1986-01-22 | 1987-08-26 | Schering Aktiengesellschaft | Insecticidal trifluormethyl alkane derivatives |
| GB2187452A (en) * | 1986-03-04 | 1987-09-09 | Ici Plc | Insecticidal fluoroalkyl benzene derivatives |
| EP0279531A2 (en) * | 1987-02-17 | 1988-08-24 | Imperial Chemical Industries Plc | Process and intermediates for the preparation of insecticidally active compounds |
-
1993
- 1993-09-29 IL IL107161A patent/IL107161A0/xx unknown
- 1993-10-14 AU AU51778/93A patent/AU5177893A/en not_active Withdrawn
- 1993-10-14 WO PCT/EP1993/002843 patent/WO1994008931A1/en active Application Filing
- 1993-10-14 MX MX9306388A patent/MX9306388A/es unknown
- 1993-10-15 TW TW082108576A patent/TW247903B/zh active
- 1993-10-15 CN CN93119131A patent/CN1090838A/zh active Pending
- 1993-10-15 ZA ZA937677A patent/ZA937677B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233834A1 (en) * | 1986-01-22 | 1987-08-26 | Schering Aktiengesellschaft | Insecticidal trifluormethyl alkane derivatives |
| GB2187452A (en) * | 1986-03-04 | 1987-09-09 | Ici Plc | Insecticidal fluoroalkyl benzene derivatives |
| EP0279531A2 (en) * | 1987-02-17 | 1988-08-24 | Imperial Chemical Industries Plc | Process and intermediates for the preparation of insecticidally active compounds |
Non-Patent Citations (1)
| Title |
|---|
| H. UNEME ET AL: "SYNTHESIS OF NON-ESTER PYRETHROIDS HAVING A 1-FLUORO-1-METHYLETHYL GROUP USING 1,2-MIGRATION OF AN ARYL GROUP", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 65, no. 9, September 1992 (1992-09-01), TOKYO JP, pages 2401 - 2410 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133279A (en) * | 1996-06-26 | 2000-10-17 | Chugai Seiyaku Kabushiki Kaisha | Therapeutic agents for renal diseases and organ preservatives |
| WO2012150206A2 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Neue cyclopropansäureeesterderivate als schädlingsbekämpfungsmittel |
| WO2012150207A1 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Verwendung von cyclopropancarbonsäureeesterderivaten zur bekämpfung von insektizid-resistenten insekten |
Also Published As
| Publication number | Publication date |
|---|---|
| IL107161A0 (en) | 1993-12-28 |
| ZA937677B (en) | 1994-05-24 |
| TW247903B (enrdf_load_stackoverflow) | 1995-05-21 |
| MX9306388A (es) | 1994-05-31 |
| CN1090838A (zh) | 1994-08-17 |
| AU5177893A (en) | 1994-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0168683B1 (de) | Flüssigkristalle mit Alkenyl- oder Alkenyloxygruppen | |
| JP5263461B2 (ja) | ２−フルオロフェニルオキシメタン構造を持つ化合物 | |
| US4528114A (en) | Acetylenes | |
| JP4288729B2 (ja) | ベンゼン誘導体およびその製造方法 | |
| CN109206384A (zh) | 基于吩噻嗪衍生物的室温磷光分子及其制备方法和应用 | |
| US4381412A (en) | 4-Fluoro-3-phenoxy-benzyl ethers | |
| US5238602A (en) | Liquid crystals | |
| US7214835B2 (en) | 1,7,8-Trifluoronaphthalene-2-naphthol, and method for producing liquid crystal compound using same | |
| WO1994008931A1 (en) | Process and intermediates for the preparation of substituted 2-phenyl-5-(3-phenoxyphenyl)-1,1,1-trifluoropentanes | |
| JP3601190B2 (ja) | アルケニルシクロヘキサン誘導体および液晶組成物 | |
| US5892131A (en) | Process for the preparation of pesticidal fluoroolefin compounds | |
| KR0166067B1 (ko) | 디사이클로헥실에틸렌 유도체 | |
| JPS58110527A (ja) | アセチレン誘導体 | |
| US5621147A (en) | Trifluoro-2-(trans-4-substituted cyclohexyl) ethylenes and process for their production | |
| JP2001252570A (ja) | キラル希土類金属触媒と不斉アルドール反応方法 | |
| JPH0653700B2 (ja) | 置換アセチレンケトン | |
| EP0811596A1 (en) | Process and intermediate compounds for the preparation of pesticidal fluoroolefin compounds | |
| CN100422126C (zh) | 生产四氢萘衍生物的方法 | |
| CA1204120A (en) | VITAMIN E INTERMEDIATES AND METHODS FOR THE PREPARATION OF (2R,4'RS,8'RS)-.alpha.-TOCOPHEROL AND (ALL-RAC)-.alpha.-TOCOPHEROL VIA THE NEW INTERMEDIATE PRODUCTS | |
| JP2857760B2 (ja) | プロポキシニトロベンゼン類の製法 | |
| JPH1025261A (ja) | フェノール誘導体の製造方法 | |
| JP4496770B2 (ja) | １−ハロゲノ−２−アルコキシナフタレン誘導体およびその製造方法 | |
| US4661640A (en) | Substituted 5-cycloalkyl-2,2-di-methyl-pentan-3-ones | |
| JPH0211572B2 (enrdf_load_stackoverflow) | ||
| JP2867368B2 (ja) | シクロヘキサノール誘導体の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU BR CA CZ FI HU JP KR PL RU SK UA US |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| WA | Withdrawal of international application | ||
| 122 | Ep: pct application non-entry in european phase | ||
| NENP | Non-entry into the national phase |
Ref country code: CA |