CN101050176A - 4-溴-2,6-二氟苯甲酸的制备方法 - Google Patents
4-溴-2,6-二氟苯甲酸的制备方法 Download PDFInfo
- Publication number
- CN101050176A CN101050176A CN 200710040525 CN200710040525A CN101050176A CN 101050176 A CN101050176 A CN 101050176A CN 200710040525 CN200710040525 CN 200710040525 CN 200710040525 A CN200710040525 A CN 200710040525A CN 101050176 A CN101050176 A CN 101050176A
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- Prior art keywords
- lithium
- difluoro
- reagent
- ether
- described step
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- 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
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- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 60
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 44
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 19
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 18
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
- 125000001979 organolithium group Chemical group 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 15
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 13
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 235000011089 carbon dioxide Nutrition 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 6
- JCIVHYBIFRUGKO-UHFFFAOYSA-N lithium;2,2,6,6-tetramethylpiperidine Chemical group [Li].CC1(C)CCCC(C)(C)N1 JCIVHYBIFRUGKO-UHFFFAOYSA-N 0.000 claims description 6
- 229940043279 diisopropylamine Drugs 0.000 claims description 5
- 239000002994 raw material Substances 0.000 abstract description 6
- IRHPJGPQWZEZRX-UHFFFAOYSA-N 4-bromo-2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=C(Br)C=C1F IRHPJGPQWZEZRX-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 32
- -1 Aromatic fluorine compound Chemical class 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000012467 final product Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000007818 Grignard reagent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000000630 rising effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 125000005190 thiohydroxy group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2007100405258A CN100522920C (zh) | 2007-05-11 | 2007-05-11 | 4-溴-2,6-二氟苯甲酸的制备方法 |
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CNB2007100405258A CN100522920C (zh) | 2007-05-11 | 2007-05-11 | 4-溴-2,6-二氟苯甲酸的制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN101050176A true CN101050176A (zh) | 2007-10-10 |
CN100522920C CN100522920C (zh) | 2009-08-05 |
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CNB2007100405258A Active CN100522920C (zh) | 2007-05-11 | 2007-05-11 | 4-溴-2,6-二氟苯甲酸的制备方法 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103012122A (zh) * | 2012-12-10 | 2013-04-03 | 天长市天佳化工科技有限公司 | 一种2-氯-5-(三氟甲基)苯甲酸的制备方法 |
CN105859543A (zh) * | 2016-05-06 | 2016-08-17 | 蚌埠中实化学技术有限公司 | 一种2,6-二氟-4-溴苯甲酰氯的制备方法 |
CN105967974A (zh) * | 2016-05-06 | 2016-09-28 | 蚌埠中实化学技术有限公司 | 一种2-甲基-3,4,5-三氟溴苯的制备方法 |
CN108003016A (zh) * | 2017-12-28 | 2018-05-08 | 上海晋鲁医药科技有限公司 | 一种2-溴-3-氟苯甲酸的合成方法 |
CN108084013A (zh) * | 2017-12-28 | 2018-05-29 | 上海晋鲁医药科技有限公司 | 一种3-溴-2-氟苯甲酸的合成方法 |
US11676615B2 (en) | 2010-08-12 | 2023-06-13 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Resampling output signals of QMF based audio codec |
CN116425623A (zh) * | 2023-04-10 | 2023-07-14 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
-
2007
- 2007-05-11 CN CNB2007100405258A patent/CN100522920C/zh active Active
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11676615B2 (en) | 2010-08-12 | 2023-06-13 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Resampling output signals of QMF based audio codec |
CN103012122A (zh) * | 2012-12-10 | 2013-04-03 | 天长市天佳化工科技有限公司 | 一种2-氯-5-(三氟甲基)苯甲酸的制备方法 |
CN103012122B (zh) * | 2012-12-10 | 2014-01-08 | 天长市天佳化工科技有限公司 | 一种2-氯-5-(三氟甲基)苯甲酸的制备方法 |
CN105859543A (zh) * | 2016-05-06 | 2016-08-17 | 蚌埠中实化学技术有限公司 | 一种2,6-二氟-4-溴苯甲酰氯的制备方法 |
CN105967974A (zh) * | 2016-05-06 | 2016-09-28 | 蚌埠中实化学技术有限公司 | 一种2-甲基-3,4,5-三氟溴苯的制备方法 |
CN108003016A (zh) * | 2017-12-28 | 2018-05-08 | 上海晋鲁医药科技有限公司 | 一种2-溴-3-氟苯甲酸的合成方法 |
CN108084013A (zh) * | 2017-12-28 | 2018-05-29 | 上海晋鲁医药科技有限公司 | 一种3-溴-2-氟苯甲酸的合成方法 |
CN108003016B (zh) * | 2017-12-28 | 2020-07-31 | 杭州逸翔化工科技有限公司 | 一种2-溴-3-氟苯甲酸的合成方法 |
CN108084013B (zh) * | 2017-12-28 | 2020-09-01 | 蓬莱市前卫化工有限公司 | 一种3-溴-2-氟苯甲酸的合成方法 |
CN116425623A (zh) * | 2023-04-10 | 2023-07-14 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
CN116425623B (zh) * | 2023-04-10 | 2024-02-13 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100522920C (zh) | 2009-08-05 |
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Assignee: Taixing Kangpeng Chemicals Co., Ltd. Assignor: Shanghai Kangpeng Chemical Co., Ltd. Contract record no.: 2011310000060 Denomination of invention: Method for preparing 4 - bromine 2,6 - difluoro benzoic acid Granted publication date: 20090805 License type: Exclusive License Open date: 20071010 Record date: 20110509 |
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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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