CN108299152A - 一种4-环丙基联苯含氟化合物的合成方法 - Google Patents
一种4-环丙基联苯含氟化合物的合成方法 Download PDFInfo
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- CN108299152A CN108299152A CN201810148479.1A CN201810148479A CN108299152A CN 108299152 A CN108299152 A CN 108299152A CN 201810148479 A CN201810148479 A CN 201810148479A CN 108299152 A CN108299152 A CN 108299152A
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- Prior art keywords
- biphenyl
- fluorochemical
- added
- reaction
- magnesium
- Prior art date
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Links
- XXIZASFJSZDZDT-UHFFFAOYSA-N 1-cyclopropyl-4-phenylbenzene Chemical group C1CC1C1=CC=C(C=2C=CC=CC=2)C=C1 XXIZASFJSZDZDT-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000010189 synthetic method Methods 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims abstract description 13
- -1 chlorine halobenzene Chemical class 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- VBBRYJMZLIYUJQ-UHFFFAOYSA-N cyclopropanone Chemical compound O=C1CC1 VBBRYJMZLIYUJQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 239000007818 Grignard reagent Substances 0.000 claims abstract 4
- 150000004795 grignard reagents Chemical class 0.000 claims abstract 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000003747 Grignard reaction Methods 0.000 claims abstract 3
- 230000018044 dehydration Effects 0.000 claims abstract 2
- 238000006297 dehydration reaction Methods 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- 239000007788 liquid Substances 0.000 claims description 29
- 238000003756 stirring Methods 0.000 claims description 23
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000011261 inert gas Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- 238000010792 warming Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 150000002940 palladium Chemical class 0.000 claims description 4
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 238000009423 ventilation Methods 0.000 claims description 3
- HXBOFIGSLNDZRW-UHFFFAOYSA-N 1-chloro-4-cyclopropylbenzene Chemical class C1=CC(Cl)=CC=C1C1CC1 HXBOFIGSLNDZRW-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 150000005171 halobenzenes Chemical class 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 239000011777 magnesium Substances 0.000 claims 8
- 229910052749 magnesium Inorganic materials 0.000 claims 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 3
- 239000003444 phase transfer catalyst Substances 0.000 claims 3
- 238000000605 extraction Methods 0.000 claims 2
- 239000011973 solid acid Substances 0.000 claims 2
- GPAKGHNMPLUSCR-UHFFFAOYSA-N 1-(cyclopenten-1-yl)-4-phenylbenzene Chemical group C1CCC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 GPAKGHNMPLUSCR-UHFFFAOYSA-N 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 230000003014 reinforcing effect Effects 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 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 238000005859 coupling reaction Methods 0.000 abstract description 4
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 3
- FPNOMFGQZWZZKJ-UHFFFAOYSA-N 1-cyclopropyl-2-phenylbenzene Chemical group C1CC1C1=CC=CC=C1C1=CC=CC=C1 FPNOMFGQZWZZKJ-UHFFFAOYSA-N 0.000 abstract 1
- NOZUZFAKEQILLQ-UHFFFAOYSA-N C1(CC1)C1=C(C=CC=C1)OB(O)O Chemical class C1(CC1)C1=C(C=CC=C1)OB(O)O NOZUZFAKEQILLQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003344 environmental pollutant Substances 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 231100000719 pollutant Toxicity 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 13
- 238000007792 addition Methods 0.000 description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000009413 insulation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000002222 fluorine compounds Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMIVDQOVSJFWOH-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=CC=C1.[F] Chemical group C1(=CC=CC=C1)C1=CC=CC=C1.[F] UMIVDQOVSJFWOH-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- HKJCELUUIFFSIN-UHFFFAOYSA-N 5-bromo-1,2,3-trifluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1F HKJCELUUIFFSIN-UHFFFAOYSA-N 0.000 description 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- DJUJYMQPXGCKHJ-UHFFFAOYSA-N C#CCCCCc(cc1)ccc1Cl Chemical compound C#CCCCCc(cc1)ccc1Cl DJUJYMQPXGCKHJ-UHFFFAOYSA-N 0.000 description 1
- 0 C*c1ccc(**c(cc2)ccc2Cl)cc1 Chemical compound C*c1ccc(**c(cc2)ccc2Cl)cc1 0.000 description 1
- OAYYRANZBHTMPN-UHFFFAOYSA-N C1(=CC=CC=C1)OB(O)O.C1=CCCC1 Chemical compound C1(=CC=CC=C1)OB(O)O.C1=CCCC1 OAYYRANZBHTMPN-UHFFFAOYSA-N 0.000 description 1
- KGUSNFKGUUFBCW-UHFFFAOYSA-N C1(CC1)C1=CC=C(C=C1)OB(O)O Chemical class C1(CC1)C1=CC=C(C=C1)OB(O)O KGUSNFKGUUFBCW-UHFFFAOYSA-N 0.000 description 1
- VNQVQUBELRFXBF-UHFFFAOYSA-N C[ClH]C1=CCC(C2(CCCCC2)O)C=C1 Chemical compound C[ClH]C1=CCC(C2(CCCCC2)O)C=C1 VNQVQUBELRFXBF-UHFFFAOYSA-N 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201810148479.1A CN108299152B (zh) | 2018-02-13 | 2018-02-13 | 一种4-环丙基联苯含氟化合物的合成方法 |
Applications Claiming Priority (1)
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CN201810148479.1A CN108299152B (zh) | 2018-02-13 | 2018-02-13 | 一种4-环丙基联苯含氟化合物的合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN108299152A true CN108299152A (zh) | 2018-07-20 |
CN108299152B CN108299152B (zh) | 2021-04-13 |
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CN201810148479.1A Active CN108299152B (zh) | 2018-02-13 | 2018-02-13 | 一种4-环丙基联苯含氟化合物的合成方法 |
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CN (1) | CN108299152B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114778714A (zh) * | 2022-03-25 | 2022-07-22 | 广东阿格蕾雅光电材料有限公司 | 一种2-二环己基膦-2’,4’,6’-三异丙基联苯gc-fid纯度分析方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101560396A (zh) * | 2009-04-10 | 2009-10-21 | 莱阳市盛华科技有限公司 | 一种含氟反式烷基环己基联苯类液晶单体的合成方法 |
CN102924243A (zh) * | 2012-03-27 | 2013-02-13 | 石家庄诚志永华显示材料有限公司 | 含有环戊基及二氟亚甲氧基连接基团的液晶化合物及其制备方法与应用 |
CN105849075A (zh) * | 2013-12-16 | 2016-08-10 | Dic株式会社 | 烯基醚化合物以及使用其的液晶组合物 |
-
2018
- 2018-02-13 CN CN201810148479.1A patent/CN108299152B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101560396A (zh) * | 2009-04-10 | 2009-10-21 | 莱阳市盛华科技有限公司 | 一种含氟反式烷基环己基联苯类液晶单体的合成方法 |
CN102924243A (zh) * | 2012-03-27 | 2013-02-13 | 石家庄诚志永华显示材料有限公司 | 含有环戊基及二氟亚甲氧基连接基团的液晶化合物及其制备方法与应用 |
CN105849075A (zh) * | 2013-12-16 | 2016-08-10 | Dic株式会社 | 烯基醚化合物以及使用其的液晶组合物 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114778714A (zh) * | 2022-03-25 | 2022-07-22 | 广东阿格蕾雅光电材料有限公司 | 一种2-二环己基膦-2’,4’,6’-三异丙基联苯gc-fid纯度分析方法 |
CN114778714B (zh) * | 2022-03-25 | 2024-03-26 | 广东阿格蕾雅光电材料有限公司 | 一种2-二环己基膦-2’,4’,6’-三异丙基联苯gc-fid纯度分析方法 |
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