CN1887833A - 1-氟萘的制备方法 - Google Patents
1-氟萘的制备方法 Download PDFInfo
- Publication number
- CN1887833A CN1887833A CN 200610028433 CN200610028433A CN1887833A CN 1887833 A CN1887833 A CN 1887833A CN 200610028433 CN200610028433 CN 200610028433 CN 200610028433 A CN200610028433 A CN 200610028433A CN 1887833 A CN1887833 A CN 1887833A
- Authority
- CN
- China
- Prior art keywords
- salt
- diazonium
- fluoronaphthalene
- acid
- diazonium fluoride
- 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.)
- Granted
Links
- CWLKTJOTWITYSI-UHFFFAOYSA-N 1-fluoronaphthalene Chemical compound C1=CC=C2C(F)=CC=CC2=C1 CWLKTJOTWITYSI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- -1 nitrous acid ester Chemical class 0.000 claims abstract description 13
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims abstract description 11
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims abstract description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012954 diazonium Substances 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 40
- FBMGKRKUOZTARV-UHFFFAOYSA-N F.OB(O)O Chemical compound F.OB(O)O FBMGKRKUOZTARV-UHFFFAOYSA-N 0.000 claims description 20
- FQKMRXHEIPOETF-UHFFFAOYSA-N F.OP(O)(O)=O Chemical compound F.OP(O)(O)=O FQKMRXHEIPOETF-UHFFFAOYSA-N 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001989 diazonium salts Chemical class 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 9
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims description 9
- 230000015556 catabolic process Effects 0.000 claims description 8
- 238000006731 degradation reaction Methods 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims description 3
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 229910020808 NaBF Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 32
- 238000002360 preparation method Methods 0.000 abstract description 11
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- WLKKCZIPYCDNLE-UHFFFAOYSA-N (4-fluoro-4-oxo-1,3,2,4lambda5-dioxazaphosphetidin-2-ium-2-ylidene)azanide Chemical compound P1(=O)(O[N+](=[N-])O1)F WLKKCZIPYCDNLE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- RHFUXPCCELGMFC-UHFFFAOYSA-N n-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-phenylmethoxyacetamide Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(=O)C)OCC1=CC=CC=C1 RHFUXPCCELGMFC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 235000010288 sodium nitrite Nutrition 0.000 description 10
- 238000001149 thermolysis Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 238000010606 normalization Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000006193 diazotization reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 230000002045 lasting effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- BFDWBSRJQZPEEB-UHFFFAOYSA-L sodium fluorophosphate Chemical compound [Na+].[Na+].[O-]P([O-])(F)=O BFDWBSRJQZPEEB-UHFFFAOYSA-L 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CNB2006100284333A CN100369874C (zh) | 2006-06-30 | 2006-06-30 | 1-氟萘的制备方法 |
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CNB2006100284333A CN100369874C (zh) | 2006-06-30 | 2006-06-30 | 1-氟萘的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN1887833A true CN1887833A (zh) | 2007-01-03 |
CN100369874C CN100369874C (zh) | 2008-02-20 |
Family
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CNB2006100284333A Active CN100369874C (zh) | 2006-06-30 | 2006-06-30 | 1-氟萘的制备方法 |
Country Status (1)
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CN (1) | CN100369874C (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101870636A (zh) * | 2010-04-01 | 2010-10-27 | 大唐(杭州)医药化工有限公司 | 2-溴-6-氟萘的制备方法 |
CN102557865A (zh) * | 2011-12-27 | 2012-07-11 | 浙江永太科技股份有限公司 | 1-氟萘的制备方法 |
CN102643160A (zh) * | 2012-04-19 | 2012-08-22 | 江苏施美康药业有限公司 | 一种1,2,4-三氟苯的制备方法 |
CN103664512A (zh) * | 2013-09-22 | 2014-03-26 | 荆楚理工学院 | 一种制备高纯度1-氟萘的方法 |
CN104447189A (zh) * | 2014-11-17 | 2015-03-25 | 武汉瑞阳化工有限公司 | 萘系含氟中间体1-氟萘的合成新方法 |
CN105753631A (zh) * | 2014-12-15 | 2016-07-13 | 沈阳化工研究院有限公司 | 一种含氟芳香族化合物的合成方法 |
CN106866350A (zh) * | 2017-04-01 | 2017-06-20 | 河北美星化工有限公司 | 一种高纯度2‑溴芴的制备方法 |
CN109180416A (zh) * | 2018-09-06 | 2019-01-11 | 武汉瑞阳化工有限公司 | 萘系含氟中间体1-氟萘的合成方法 |
CN112778075A (zh) * | 2021-02-01 | 2021-05-11 | 李佰卫 | 一种1-氟萘的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2269561C (en) * | 1998-04-22 | 2007-06-05 | Dainippon Ink And Chemicals, Inc. | Naphthalene derivative and liquid crystal composition comprising the same |
-
2006
- 2006-06-30 CN CNB2006100284333A patent/CN100369874C/zh active Active
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101870636A (zh) * | 2010-04-01 | 2010-10-27 | 大唐(杭州)医药化工有限公司 | 2-溴-6-氟萘的制备方法 |
CN101870636B (zh) * | 2010-04-01 | 2013-01-23 | 大唐(杭州)医药化工有限公司 | 2-溴-6-氟萘的制备方法 |
CN102557865A (zh) * | 2011-12-27 | 2012-07-11 | 浙江永太科技股份有限公司 | 1-氟萘的制备方法 |
CN102557865B (zh) * | 2011-12-27 | 2014-03-12 | 浙江永太科技股份有限公司 | 1-氟萘的制备方法 |
CN102643160A (zh) * | 2012-04-19 | 2012-08-22 | 江苏施美康药业有限公司 | 一种1,2,4-三氟苯的制备方法 |
CN103664512A (zh) * | 2013-09-22 | 2014-03-26 | 荆楚理工学院 | 一种制备高纯度1-氟萘的方法 |
CN104447189A (zh) * | 2014-11-17 | 2015-03-25 | 武汉瑞阳化工有限公司 | 萘系含氟中间体1-氟萘的合成新方法 |
CN105753631A (zh) * | 2014-12-15 | 2016-07-13 | 沈阳化工研究院有限公司 | 一种含氟芳香族化合物的合成方法 |
CN105753631B (zh) * | 2014-12-15 | 2018-11-02 | 沈阳化工研究院有限公司 | 一种含氟芳香族化合物的合成方法 |
CN106866350A (zh) * | 2017-04-01 | 2017-06-20 | 河北美星化工有限公司 | 一种高纯度2‑溴芴的制备方法 |
CN106866350B (zh) * | 2017-04-01 | 2019-06-11 | 宁夏中星显示材料有限公司 | 一种高纯度2-溴芴的制备方法 |
CN109180416A (zh) * | 2018-09-06 | 2019-01-11 | 武汉瑞阳化工有限公司 | 萘系含氟中间体1-氟萘的合成方法 |
CN112778075A (zh) * | 2021-02-01 | 2021-05-11 | 李佰卫 | 一种1-氟萘的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100369874C (zh) | 2008-02-20 |
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Assignee: Zhejiang Huajing Fluorine Chemistry Technology Co., Ltd. Assignor: Shanghai Kangpeng Chemical Co., Ltd. Contract record no.: 2010990000752 Denomination of invention: Prepn process of 1-fluoronaphthalene Granted publication date: 20080220 License type: Exclusive License Open date: 20070103 Record date: 20100916 |
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Address after: 2003 No. 3, Lane 1273, Tongpu Road, Putuo District, Shanghai Patentee after: Shanghai Kangpeng Science and Technology Co., Ltd. Address before: 2003 No. 3, Lane 1273, Tongpu Road, Putuo District, Shanghai Patentee before: Shanghai Kangpeng Chemical Co., Ltd. |
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Change date: 20190625 Contract record no.: 2010990000752 Assignor after: Shanghai Kangpeng Science and Technology Co., Ltd. Assignor before: Shanghai Kangpeng Chemical Co., Ltd. |
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Assignee: Zhejiang Huajing Fluorine Chemistry Technology Co., Ltd. Assignor: Shanghai Kangpeng Science and Technology Co., Ltd. Contract record no.: 2010990000752 Date of cancellation: 20190703 |