JPH0672112B2 - 新規なビスベンゾトリフルオリド誘導体およびその製造法 - Google Patents
新規なビスベンゾトリフルオリド誘導体およびその製造法Info
- Publication number
- JPH0672112B2 JPH0672112B2 JP62100024A JP10002487A JPH0672112B2 JP H0672112 B2 JPH0672112 B2 JP H0672112B2 JP 62100024 A JP62100024 A JP 62100024A JP 10002487 A JP10002487 A JP 10002487A JP H0672112 B2 JPH0672112 B2 JP H0672112B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- trifluoromethylphenyl
- ccl
- derivative
- bisbenzotrifluoride
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical class FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- OVUAUGZRYXICFV-UHFFFAOYSA-N 1-(trifluoromethyl)-2-[2-[2-(trifluoromethyl)phenyl]ethynyl]benzene Chemical group FC(F)(F)C1=CC=CC=C1C#CC1=CC=CC=C1C(F)(F)F OVUAUGZRYXICFV-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VDEUYVGUNSJXAE-UHFFFAOYSA-N 1-(trichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)(Cl)Cl VDEUYVGUNSJXAE-UHFFFAOYSA-N 0.000 description 3
- QCNIMLJOVLXUSO-UHFFFAOYSA-N 1-(trifluoromethyl)-2-[1-[2-(trifluoromethyl)phenyl]ethyl]benzene Chemical compound FC(F)(F)C1=C(C=CC=C1)C(C)C1=C(C=CC=C1)C(F)(F)F QCNIMLJOVLXUSO-UHFFFAOYSA-N 0.000 description 3
- LZRAUNCUFOGKDN-UHFFFAOYSA-N 1-(trifluoromethyl)-2-[2-[2-(trifluoromethyl)phenyl]ethenyl]benzene Chemical group FC(F)(F)C1=CC=CC=C1C=CC1=CC=CC=C1C(F)(F)F LZRAUNCUFOGKDN-UHFFFAOYSA-N 0.000 description 3
- JVPNVOZUSGFXEC-UHFFFAOYSA-N 1-[1,1,2,2-tetrachloro-2-[3-(trifluoromethyl)phenyl]ethyl]-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(Cl)C(Cl)(Cl)C=2C=C(C=CC=2)C(F)(F)F)=C1 JVPNVOZUSGFXEC-UHFFFAOYSA-N 0.000 description 3
- IQHBDRUNRCUWNS-UHFFFAOYSA-N 1-[1,2-dichloro-2-[2-(trifluoromethyl)phenyl]ethenyl]-2-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=C(C=CC=C1)C(=C(Cl)C1=C(C=CC=C1)C(F)(F)F)Cl IQHBDRUNRCUWNS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- QEQNRERDWZEPBB-UHFFFAOYSA-N 1-[1,2,2,2-tetrachloro-1-[2-(trifluoromethyl)phenyl]ethyl]-2-(trifluoromethyl)benzene Chemical compound FC(C1=C(C=CC=C1)C(C(Cl)(Cl)Cl)(Cl)C1=C(C=CC=C1)C(F)(F)F)(F)F QEQNRERDWZEPBB-UHFFFAOYSA-N 0.000 description 2
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 trifluoromethylphenyl Chemical group 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- XGIRWNFILAXTJE-UHFFFAOYSA-N 1,2-dichloro-3-(fluoromethyl)-4-(trifluoromethyl)benzene Chemical compound ClC1=C(C(=C(C=C1)C(F)(F)F)CF)Cl XGIRWNFILAXTJE-UHFFFAOYSA-N 0.000 description 1
- SKWWCKGHUDPXOZ-UHFFFAOYSA-N 1-(trichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(Cl)Cl)=C1 SKWWCKGHUDPXOZ-UHFFFAOYSA-N 0.000 description 1
- NTFZDVDWIVFEEI-UHFFFAOYSA-N 1-(trichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)(Cl)Cl)C=C1 NTFZDVDWIVFEEI-UHFFFAOYSA-N 0.000 description 1
- DVTDJNNYVSWCNP-UHFFFAOYSA-N 1-(trifluoromethyl)-3-[2-[3-(trifluoromethyl)phenyl]ethynyl]benzene Chemical group FC(F)(F)C1=CC=CC(C#CC=2C=C(C=CC=2)C(F)(F)F)=C1 DVTDJNNYVSWCNP-UHFFFAOYSA-N 0.000 description 1
- JCSXFQUFCSSRSY-UHFFFAOYSA-N 1-[1,2-dichloro-2-[3-(trifluoromethyl)phenyl]ethenyl]-3-(trifluoromethyl)benzene Chemical group FC(C=1C=C(C=CC=1)C(=C(Cl)C1=CC(=CC=C1)C(F)(F)F)Cl)(F)F JCSXFQUFCSSRSY-UHFFFAOYSA-N 0.000 description 1
- AJRORQBMERVXTE-UHFFFAOYSA-N 1-[1,2-dichloro-2-[4-(trifluoromethyl)phenyl]ethenyl]-4-(trifluoromethyl)benzene Chemical group C1=CC(C(F)(F)F)=CC=C1C(Cl)=C(Cl)C1=CC=C(C(F)(F)F)C=C1 AJRORQBMERVXTE-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000007193 benzoin condensation reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62100024A JPH0672112B2 (ja) | 1987-04-24 | 1987-04-24 | 新規なビスベンゾトリフルオリド誘導体およびその製造法 |
| GB8809137A GB2204313B (en) | 1987-04-24 | 1988-04-18 | Novel bisbenzotrifluoride derivatives and method of preparing same |
| IT20278/88A IT1218225B (it) | 1987-04-24 | 1988-04-21 | Derivati del bisbenzotrifluoruro e metodo di preparazione degli stessi |
| DE3813453A DE3813453A1 (de) | 1987-04-24 | 1988-04-21 | Neue bisbenzotrifluoridderivate und verfahren zu ihrer herstellung |
| FR8805400A FR2614296B1 (fr) | 1987-04-24 | 1988-04-22 | Nouveaux derives de bisbenzotrifluorures et procede pour leur preparation. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62100024A JPH0672112B2 (ja) | 1987-04-24 | 1987-04-24 | 新規なビスベンゾトリフルオリド誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63267737A JPS63267737A (ja) | 1988-11-04 |
| JPH0672112B2 true JPH0672112B2 (ja) | 1994-09-14 |
Family
ID=14262971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62100024A Expired - Lifetime JPH0672112B2 (ja) | 1987-04-24 | 1987-04-24 | 新規なビスベンゾトリフルオリド誘導体およびその製造法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH0672112B2 (enrdf_load_stackoverflow) |
| DE (1) | DE3813453A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2614296B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2204313B (enrdf_load_stackoverflow) |
| IT (1) | IT1218225B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918251A (en) * | 1989-04-04 | 1990-04-17 | Mallinckrodt, Inc. | Preparation of 2-halofluorobenzene |
| JP3008510B2 (ja) * | 1991-02-16 | 2000-02-14 | ダイキン工業株式会社 | 含フッ素エタンの２量体の製法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2644835A (en) * | 1947-06-05 | 1953-07-07 | Us Rubber Co | Coupled products |
| GB1265051A (enrdf_load_stackoverflow) * | 1968-03-13 | 1972-03-01 | ||
| IT1125157B (it) * | 1976-11-19 | 1986-05-14 | Sarda Off Mec | Procedimento per la preparazione di composti,'-dialogeno etilaromatici |
| US4634797A (en) * | 1985-02-07 | 1987-01-06 | Halocarbon Products Corporation | Coupling of chloroperfluoroalkanes |
-
1987
- 1987-04-24 JP JP62100024A patent/JPH0672112B2/ja not_active Expired - Lifetime
-
1988
- 1988-04-18 GB GB8809137A patent/GB2204313B/en not_active Expired - Fee Related
- 1988-04-21 DE DE3813453A patent/DE3813453A1/de active Granted
- 1988-04-21 IT IT20278/88A patent/IT1218225B/it active
- 1988-04-22 FR FR8805400A patent/FR2614296B1/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2614296B1 (fr) | 1990-06-15 |
| IT1218225B (it) | 1990-04-12 |
| FR2614296A1 (fr) | 1988-10-28 |
| GB2204313A (en) | 1988-11-09 |
| DE3813453A1 (de) | 1988-11-03 |
| DE3813453C2 (enrdf_load_stackoverflow) | 1993-06-09 |
| GB8809137D0 (en) | 1988-05-18 |
| IT8820278A0 (it) | 1988-04-21 |
| JPS63267737A (ja) | 1988-11-04 |
| GB2204313B (en) | 1990-10-31 |
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