CN104151130B - 一种制备高纯度4-溴芴的方法 - Google Patents
一种制备高纯度4-溴芴的方法 Download PDFInfo
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- CN104151130B CN104151130B CN201410337630.8A CN201410337630A CN104151130B CN 104151130 B CN104151130 B CN 104151130B CN 201410337630 A CN201410337630 A CN 201410337630A CN 104151130 B CN104151130 B CN 104151130B
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- CN
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- Prior art keywords
- butyl
- fluorenes
- purity
- tert
- bromine fluorenes
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 19
- 239000012043 crude product Substances 0.000 claims abstract description 16
- 150000002220 fluorenes Chemical class 0.000 claims abstract description 12
- DFZYPLLGAQIQTD-UHFFFAOYSA-N 2,7-ditert-butyl-9h-fluorene Chemical compound CC(C)(C)C1=CC=C2C3=CC=C(C(C)(C)C)C=C3CC2=C1 DFZYPLLGAQIQTD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019441 ethanol Nutrition 0.000 claims abstract description 11
- 238000001953 recrystallisation Methods 0.000 claims abstract description 11
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims abstract description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 layering Substances 0.000 claims description 11
- 150000001649 bromium compounds Chemical class 0.000 claims description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000004807 desolvation Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000010813 municipal solid waste Substances 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- CYWOYTTVDRIHPW-UHFFFAOYSA-M CC[N+](CC)(CC)CC1=CC=CC=C1.N.[Br-].Br.Br Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1.N.[Br-].Br.Br CYWOYTTVDRIHPW-UHFFFAOYSA-M 0.000 claims description 2
- LCKDOHRDONNZTG-UHFFFAOYSA-N 1,2-dibromo-9h-fluorene Chemical class C1=CC=C2CC3=C(Br)C(Br)=CC=C3C2=C1 LCKDOHRDONNZTG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 2
- 239000002841 Lewis acid Substances 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 150000007517 lewis acids Chemical class 0.000 abstract description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 3
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IVCIRNMUSNCCKD-UHFFFAOYSA-N Brc(cccc1)c1-c1ccccc1C1C=CC=CC=C1 Chemical compound Brc(cccc1)c1-c1ccccc1C1C=CC=CC=C1 IVCIRNMUSNCCKD-UHFFFAOYSA-N 0.000 description 1
- XFWGSCNZZYLJJG-UHFFFAOYSA-N Brc1c2-c3ccccc3Cc2ccc1 Chemical compound Brc1c2-c3ccccc3Cc2ccc1 XFWGSCNZZYLJJG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000002305 electric material Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN201410337630.8A CN104151130B (zh) | 2014-07-15 | 2014-07-15 | 一种制备高纯度4-溴芴的方法 |
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CN201410337630.8A CN104151130B (zh) | 2014-07-15 | 2014-07-15 | 一种制备高纯度4-溴芴的方法 |
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CN104151130A CN104151130A (zh) | 2014-11-19 |
CN104151130B true CN104151130B (zh) | 2016-04-06 |
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CN109836425B (zh) * | 2017-11-24 | 2023-01-24 | 江苏创诺制药有限公司 | 一种合成培美酸的制备工艺 |
CN109665938A (zh) * | 2018-12-18 | 2019-04-23 | 河南省科学院化学研究所有限公司 | 一种4-溴-9-甲基-9'-苯基芴的生产方法 |
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JP6430367B2 (ja) * | 2012-04-17 | 2018-11-28 | メルク パテント ゲーエムベーハー | 架橋結合可能なおよび架橋結合されたポリマー、その製造方法およびその使用 |
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Address after: 264006 Shandong city of Yantai Province Economic and Technological Development Zone Wuzhi Mountain Road No. 11 Applicant after: VALIANT Co.,Ltd. Address before: 264006 Shandong city of Yantai Province Economic and Technological Development Zone Wuzhi Mountain Road No. 11 Applicant before: Yantai Valiant Fine Chemicals Co.,Ltd. |
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Denomination of invention: A method for preparing high purity 4-bromofluorene Effective date of registration: 20211202 Granted publication date: 20160406 Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd. Pledgor: VALIANT Co.,Ltd. Registration number: Y2021980013807 |
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Date of cancellation: 20220823 Granted publication date: 20160406 Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd. Pledgor: VALIANT Co.,Ltd. Registration number: Y2021980013807 |