CN102766073A - 一种间三氟甲基苯对氰基苯乙酮的合成方法 - Google Patents
一种间三氟甲基苯对氰基苯乙酮的合成方法 Download PDFInfo
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- CN102766073A CN102766073A CN2012102726131A CN201210272613A CN102766073A CN 102766073 A CN102766073 A CN 102766073A CN 2012102726131 A CN2012102726131 A CN 2012102726131A CN 201210272613 A CN201210272613 A CN 201210272613A CN 102766073 A CN102766073 A CN 102766073A
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- Prior art keywords
- solvent
- acetylbenzonitrile
- compound method
- reaction
- trifluoromethyl benzene
- Prior art date
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- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 43
- -1 m-benzenyl trifluoride Chemical compound 0.000 title abstract 3
- QILKKAFYAFEWGU-UHFFFAOYSA-N 4-(cyanomethyl)benzonitrile Chemical compound N#CCC1=CC=C(C#N)C=C1 QILKKAFYAFEWGU-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 27
- 238000003756 stirring Methods 0.000 claims description 27
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 26
- 229940073608 benzyl chloride Drugs 0.000 claims description 26
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 23
- HDPVZMJMBJNVEH-UHFFFAOYSA-N C(C)(=O)C1=CC=C(C#N)C=C1.FC(C=1C=CC=CC1)(F)F Chemical compound C(C)(=O)C1=CC=C(C#N)C=C1.FC(C=1C=CC=CC1)(F)F HDPVZMJMBJNVEH-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 20
- 229960001701 chloroform Drugs 0.000 claims description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 18
- 239000010410 layer Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 16
- 239000007810 chemical reaction solvent Substances 0.000 claims description 14
- QQHNNQCWKYFNAC-UHFFFAOYSA-N methyl 3-(trifluoromethyl)benzoate Chemical class COC(=O)C1=CC=CC(C(F)(F)F)=C1 QQHNNQCWKYFNAC-UHFFFAOYSA-N 0.000 claims description 12
- 238000010792 warming Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 9
- 238000004811 liquid chromatography Methods 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 238000010606 normalization Methods 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- 238000001953 recrystallisation Methods 0.000 claims description 9
- 238000007789 sealing Methods 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000007255 decyanation reaction Methods 0.000 claims description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 5
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 238000005070 sampling Methods 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 2
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 abstract description 9
- 239000005914 Metaflumizone Substances 0.000 abstract description 9
- 239000002917 insecticide Substances 0.000 abstract description 5
- LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 4
- 0 C*C(CC1)C1C1CCC(CCC=*)CC1 Chemical compound C*C(CC1)C1C1CCC(CCC=*)CC1 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 150000007659 semicarbazones Chemical class 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000931705 Cicada Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106349006A (zh) * | 2016-08-26 | 2017-01-25 | 大连奇凯医药科技有限公司 | 3‑三氟甲基苯乙腈的制备方法 |
CN109180529A (zh) * | 2018-10-24 | 2019-01-11 | 徐州伯利恒生物科技有限公司 | 一种农药中间体4-氰基苯乙腈的合成方法 |
CN109336785A (zh) * | 2018-10-24 | 2019-02-15 | 徐州伯利恒生物科技有限公司 | 一种离子液体催化剂及其在合成4-氰基苯乙腈的应用 |
CN112939738A (zh) * | 2021-01-29 | 2021-06-11 | 杭州凯方科技有限公司 | 一种3,5-二羟基戊苯的制备方法 |
Citations (2)
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CN101386590A (zh) * | 2007-09-13 | 2009-03-18 | 中国医学科学院药物研究所 | 含有羟甲基和羧基的吡咯烷酮、制法及药物组合物与用途 |
CN101715774A (zh) * | 2008-10-09 | 2010-06-02 | 浙江化工科技集团有限公司 | 一个具有杀虫活性化合物制备及用途 |
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2012
- 2012-08-02 CN CN201210272613.1A patent/CN102766073B/zh active Active
Patent Citations (2)
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CN101386590A (zh) * | 2007-09-13 | 2009-03-18 | 中国医学科学院药物研究所 | 含有羟甲基和羧基的吡咯烷酮、制法及药物组合物与用途 |
CN101715774A (zh) * | 2008-10-09 | 2010-06-02 | 浙江化工科技集团有限公司 | 一个具有杀虫活性化合物制备及用途 |
Non-Patent Citations (4)
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《Tetrahedron》 20061231 Hosuk Ryu et al. Photo- and electroluminescent properties of cyano-substituted styryl derivatives and synthesis of CN-PPV model compounds containing an alkoxy spacer for OLEDs 6236-6247 1-10 第62卷, * |
HOSUK RYU ET AL.: "Photo- and electroluminescent properties of cyano-substituted styryl derivatives and synthesis of CN–PPV model compounds containing an alkoxy spacer for OLEDs", 《TETRAHEDRON》 * |
JOHN W. BUNTING ET AL.: "Equilibrium and Kinetic Acidities of Benzylic Ketones. Application of the Marcus Equation to the Deprotonation of Carbon Acids", 《J. AM. CHEM. SOC.》 * |
MANDAN CHIDAMBARAM ET AL.: "Didecyldimethylammonium bromide (DDAB): a universal, robust,and highly potent phase-transfer catalyst for diverse organic transformations", 《TETRAHEDRON》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106349006A (zh) * | 2016-08-26 | 2017-01-25 | 大连奇凯医药科技有限公司 | 3‑三氟甲基苯乙腈的制备方法 |
CN106349006B (zh) * | 2016-08-26 | 2019-02-05 | 大连奇凯医药科技有限公司 | 3-三氟甲基苯乙腈的制备方法 |
CN109180529A (zh) * | 2018-10-24 | 2019-01-11 | 徐州伯利恒生物科技有限公司 | 一种农药中间体4-氰基苯乙腈的合成方法 |
CN109336785A (zh) * | 2018-10-24 | 2019-02-15 | 徐州伯利恒生物科技有限公司 | 一种离子液体催化剂及其在合成4-氰基苯乙腈的应用 |
CN112939738A (zh) * | 2021-01-29 | 2021-06-11 | 杭州凯方科技有限公司 | 一种3,5-二羟基戊苯的制备方法 |
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