CN103787846A - 一种2-氯-6-氟苯甲醚及其中间体的制备方法 - Google Patents
一种2-氯-6-氟苯甲醚及其中间体的制备方法 Download PDFInfo
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- CN103787846A CN103787846A CN201410084371.2A CN201410084371A CN103787846A CN 103787846 A CN103787846 A CN 103787846A CN 201410084371 A CN201410084371 A CN 201410084371A CN 103787846 A CN103787846 A CN 103787846A
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000006266 etherification reaction Methods 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 238000006722 reduction reaction Methods 0.000 claims abstract description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 18
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 21
- QASFEHCRPLPGES-UHFFFAOYSA-N 1-chloro-3-fluoro-2-methoxybenzene Chemical compound COC1=C(F)C=CC=C1Cl QASFEHCRPLPGES-UHFFFAOYSA-N 0.000 claims description 14
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 13
- 238000010504 bond cleavage reaction Methods 0.000 claims description 12
- 238000006193 diazotization reaction Methods 0.000 claims description 12
- 230000007017 scission Effects 0.000 claims description 12
- 238000006482 condensation reaction Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- 229940043279 diisopropylamine Drugs 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 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 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 235000010289 potassium nitrite Nutrition 0.000 claims description 2
- 239000004304 potassium nitrite Substances 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000009413 insulation Methods 0.000 description 19
- 238000010792 warming Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 11
- 238000005070 sampling Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 6
- 238000004807 desolvation Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000005251 gamma ray Effects 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- QIAQIYQASAWZPP-UHFFFAOYSA-N 2-chloro-6-fluorophenol Chemical compound OC1=C(F)C=CC=C1Cl QIAQIYQASAWZPP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- MSBUQNLLSANFDL-UHFFFAOYSA-N COc(c([N+]([O-])=O)ccc1)c1Cl Chemical compound COc(c([N+]([O-])=O)ccc1)c1Cl MSBUQNLLSANFDL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical group OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- VPZJHTWLWKFPQW-UHFFFAOYSA-N COc(c(Cl)ccc1)c1N Chemical compound COc(c(Cl)ccc1)c1N VPZJHTWLWKFPQW-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000006350 Schiemann fluorination reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- 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
- C07F5/022—Boron compounds without C-boron linkages
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- 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)
Abstract
Description
Claims (13)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410084371.2A CN103787846B (zh) | 2014-03-07 | 2014-03-07 | 一种2-氯-6-氟苯甲醚及其中间体的制备方法 |
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CN201410084371.2A CN103787846B (zh) | 2014-03-07 | 2014-03-07 | 一种2-氯-6-氟苯甲醚及其中间体的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN103787846A true CN103787846A (zh) | 2014-05-14 |
CN103787846B CN103787846B (zh) | 2016-01-27 |
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CN201410084371.2A Active CN103787846B (zh) | 2014-03-07 | 2014-03-07 | 一种2-氯-6-氟苯甲醚及其中间体的制备方法 |
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CN (1) | CN103787846B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116120145A (zh) * | 2022-12-15 | 2023-05-16 | 浙江工业大学 | 一种2-氯-3-氟甲苯的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4476320A (en) * | 1981-10-21 | 1984-10-09 | Bayer Aktiengesellschaft | Process for the preparation of fluoroaromatic compounds substituted in the o-position |
-
2014
- 2014-03-07 CN CN201410084371.2A patent/CN103787846B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4476320A (en) * | 1981-10-21 | 1984-10-09 | Bayer Aktiengesellschaft | Process for the preparation of fluoroaromatic compounds substituted in the o-position |
Non-Patent Citations (2)
Title |
---|
周小建等: "相转移催化合成2,4-二甲氧基硝基苯的研究", 《染料工业》, vol. 31, no. 6, 31 December 1994 (1994-12-31), pages 23 - 27 * |
李华: "配位改性的Pt/C催化剂高选择性加氢合成3-氯-2-甲基苯胺", 《化学工业与工程技术》, vol. 33, no. 1, 29 February 2012 (2012-02-29), pages 11 - 13 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116120145A (zh) * | 2022-12-15 | 2023-05-16 | 浙江工业大学 | 一种2-氯-3-氟甲苯的制备方法 |
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CN103787846B (zh) | 2016-01-27 |
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Address after: 224631 Jiangsu Province, Yancheng City Chemical Industry Park Applicant after: JIANGSU LIANHUA TECHNOLOGY Co.,Ltd. Applicant after: LIANHE CHEMICAL TECHNOLOGY (YANCHENG) Co.,Ltd. Applicant after: LIANHE CHEMICAL TECHNOLOGY (SHANGHAI) Co.,Ltd. Address before: 200120 Shanghai Kang Xin Road, Lane 3399, No. 1, No. 9, Pudong New Area Applicant before: LIANHE CHEMICAL TECHNOLOGY (SHANGHAI) Co.,Ltd. Applicant before: LIANHE CHEMICAL TECHNOLOGY (YANCHENG) Co.,Ltd. Applicant before: JIANGSU LIANHUA TECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20220823 Address after: 224631 In Chenjiagang Chemical Industry Park, Xiangshui County, Yancheng City, Jiangsu Province Patentee after: JIANGSU LIANHUA TECHNOLOGY Co.,Ltd. Patentee after: LIANHE CHEMICAL TECHNOLOGY (SHANGHAI) Co.,Ltd. Address before: 224631 Chenjiagang Chemical Industry Park, Xiangshui County, Yancheng City, Jiangsu Province Patentee before: JIANGSU LIANHUA TECHNOLOGY Co.,Ltd. Patentee before: LIANHE CHEMICAL TECHNOLOGY (YANCHENG) Co.,Ltd. Patentee before: LIANHE CHEMICAL TECHNOLOGY (SHANGHAI) Co.,Ltd. |
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Effective date of registration: 20221122 Address after: 318020 No. 8, yongjiao Road, Jiangkou street, Huangyan District, Taizhou City, Zhejiang Province Patentee after: Lianhua angjian Pharmaceutical (Taizhou) Co.,Ltd. Address before: 224631 In Chenjiagang Chemical Industry Park, Xiangshui County, Yancheng City, Jiangsu Province Patentee before: JIANGSU LIANHUA TECHNOLOGY Co.,Ltd. Patentee before: LIANHE CHEMICAL TECHNOLOGY (SHANGHAI) Co.,Ltd. |