CN105859761A - Synthesis method of aromatic borate compounds - Google Patents
Synthesis method of aromatic borate compounds Download PDFInfo
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- CN105859761A CN105859761A CN201610264971.6A CN201610264971A CN105859761A CN 105859761 A CN105859761 A CN 105859761A CN 201610264971 A CN201610264971 A CN 201610264971A CN 105859761 A CN105859761 A CN 105859761A
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- reaction tube
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- acid ester
- boric acid
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- -1 aromatic borate compounds Chemical class 0.000 title claims abstract description 23
- 238000001308 synthesis method Methods 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004440 column chromatography Methods 0.000 claims abstract description 7
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 6
- 239000003208 petroleum Substances 0.000 claims abstract description 3
- 239000002131 composite material Substances 0.000 claims description 11
- 230000004044 response Effects 0.000 claims description 7
- 230000006837 decompression Effects 0.000 claims description 6
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 238000010189 synthetic method Methods 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 10
- 238000003756 stirring Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000003480 eluent Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000005311 nuclear magnetism Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DAJLHNABGVYSOO-UHFFFAOYSA-N boric acid;2,3-dimethylbutane-2,3-diol Chemical compound OB(O)O.CC(C)(O)C(C)(C)O DAJLHNABGVYSOO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of aromatic borate compounds, belonging to the technical field of chemical synthesis of intermediates. The method particularly comprises the following steps: (1) adding acetonitrile, aryl sulfonyl chloride, pinacone biborate and dipotassium hydrogen phosphate into a reaction tube, tightening the plug of the reaction tube, and carrying out reaction at room temperature in the reaction tube under the irradiation of an ultraviolet lamp for 24 hours while magnetically stirring; and (2) after the reaction finishes, evaporating under reduced pressure to remove most of the solvent, carrying out separation purification on the residual mixed solution by column chromatography by using an eluent composed of petroleum ether and ethyl acetate in a volume ratio of 10:1-30:1, thereby obtaining the product. The method has wide applicability in the fields of organic synthesis, materials, medicine, pesticides and the like. The method has the advantages of low cost, high yield and the like, is simple to operate, and thus, has favorable application prospects.
Description
Technical field
The invention belongs to organic synthesis intermediate technical field, be specifically related to one and utilize UV light-induced synthesis fragrance boron
The method of ester compound.
Background technology
Aromatic boronic acid ester composite is very important intermediate in organic synthesis, is widely used in suzuki etc. and intersects even
Connection reaction.The traditional preparation methods of aryl-boric acid ester is RMgBr or organolithium reagent reacts with trialkylboron ester, through hydrolysis
Resterification.But the method has certain limitation, need low temperature and the condition of strict anhydrous and oxygen-free, and functional group tolerance is poor.
In recent years, the aromatic boronic acid ester composite synthetic method of document report has a lot.Transition metal-catalyzed aryl halogenation
Thing is to synthesize the classical way of this compounds with the coupling reaction of connection boric acid pinacol ester.The advantage that this method is maximum
It is applicability widely, and easy and simple to handle, it is not required to strict anhydrous and oxygen-free condition.But also there are some shortcomings, such as your gold
Belonging to the use of palladium catalyst and cannot avoid the residual of transition metal, this problem shows particularly in drug molecule synthesizes
Prominent.It addition, it is a kind of brand-new for utilizing the direct boronation reaction of transition metal (rhodium or iridium catalyst) catalyzing aromatic hydrocarbon carbon-hydrogen link
Synthesizing aryl boric acid ester compound method.Such reaction embodies the feature such as Green Chemistry, Atom economy, the region choosing of reaction
Selecting property mainly by steric hindrance control, obtains the boronation product based on meta.But, such reaction needs for utilizing expensive mistake
Cross the reaction condition of metallic catalyst and harshness.Recently, document reports a kind of without metal participation, with benzene cheap and easy to get
Amine one step can synthesize aromatic boronic acid ester composite.The condition of this reaction is as mild as a dove, it might even be possible to carry out anti-under air conditions
Should, and participate in without metal, the problem that so can avoid metal residual.Subsequently, organic photosensitive agent is utilized to be catalyzed aromatic diazo salt
Boronation reaction also can synthesize this compounds.But, aromatic diazo salt compound is not sufficiently stable, and is not suitable for producing in a large number, and not
Easily preserve.Although the mechanism of such reaction is also not very clear, it may be possible to experienced by free radical mechanism.
It is contemplated that the aryl sulfonyl chloride in reaction system, connection boric acid pinacol ester, under conditions of light-initiated, occurs certainly
Aromatic boronic acid ester composite is built by base coupling reaction.This response strategy has certain challenge.Up to now, not yet have
Document is reported.
Summary of the invention
The technical problem to be solved is: the deficiency existed for prior art, it is provided that a kind of low cost, productivity
The high method utilizing free radical coupling reaction synthesis aromatic boronic acid ester composite.
For realizing the purpose of the present invention, it is achieved by the following technical solutions: a kind of aromatic boronic acid ester composite synthesis
Method,
Reaction equation is
Specifically include following steps:
1. in reaction tube, add acetonitrile, aryl sulfonyl chloride, connection boric acid pinacol ester and dipotassium hydrogen phosphate, tighten reaction tube
Stopper, use ultra violet lamp reaction tube, at room temperature magnetic agitation is reacted 24 hours；
2. after question response terminates, decompression boils off major part solvent, with volume ratio as 10:1～the petroleum ether of 30:1 and acetic acid
Ethyl ester is that leacheate carries out column chromatography for separation purification to remaining mixed liquor, obtains product.
As preferably: aryl sulfonyl chloride and connection boric acid pinacol ester free radical coupling in reaction.
Compared with prior art, the invention has the beneficial effects as follows: the present invention uses the aryl sulfonyl chloride cheap and easy to get to be
Raw material, can be efficiently synthesized a series of aromatic boronic acid ester composite through UV light-induced.The compound of the present invention can be used as
Organic synthesis intermediate and having a wide range of applications at numerous areas such as material, medicine, agricultural chemicals.The present invention is even by free radical
Connection is synthesized aromatic boronic acid ester composite.Compared with existing synthetic method, the inventive method operation is simple, raw materials used warp
Helping, be easy to get, productivity is higher.
Detailed description of the invention
Embodiment 1: the synthesis of borate ester
Acetonitrile 2mL, benzene sulfonyl chloride (52.8mg, 0.3mmol), connection boric acid pinacol ester is added in 25mL reaction tube
(114.3mg, 0.45mmol), dipotassium hydrogen phosphate (104.4mg, 2.0eq.), use ultra violet lamp reaction tube, at room temperature magnetic force
Stirring reaction 24 hours.After question response terminates, decompression boils off major part solvent, with petrol ether/ethyl acetate (30:1) as drip washing
Liquid carries out column chromatography for separation purification to remaining mixed liquor, obtains required product, for white solid, 39.8mg, yield 65%.
Its nuclear-magnetism modal data is as follows:
1H NMR(300MHz,CDCl3) δ=7.94～7.90 (m, 1H), 7.84 (d, J=6.0Hz, 1H), 7.64 (d, J=
6.0Hz, 1H), 7.50～7.28 (m, 2H), 1.37 (s, 12H).13C NMR(75MHz,CDCl3) δ=137.6,134.7,
131.2,127.7,127.1,83.8,24.9.
The synthesis of embodiment 2:4-methylphenylboronic acid ester
Acetonitrile 2mL, 4-toluene sulfonyl chloride (57.0mg, 0.3mmol), connection boric acid pinacol is added in 25mL reaction tube
Ester (114.3mg, 0.45mmol), dipotassium hydrogen phosphate (104.4mg, 2.0eq.), use ultra violet lamp reaction tube, at room temperature magnetic
Power stirring reaction 24 hours.After question response terminates, decompression boils off major part solvent, with petrol ether/ethyl acetate (30:1) for drenching
Washing lotion carries out column chromatography for separation purification to remaining mixed liquor, obtains required product, for white solid, 44.5mg, yield 68%.
Its nuclear-magnetism modal data is as follows:
1H NMR(300MHz,CDCl3) δ=7.81 (d, J=9.0Hz, 2H), 7.27 (d, J=9.0Hz, 2H), 2.44 (s,
3H),1.41(s,12H).13C NMR(75MHz,CDCl3) δ=141.4,134.9,128.6,83.6,24.9,21.8.
The synthesis of embodiment 3:4-methoxyphenylboronic acid ester
Acetonitrile 2mL, 4-toluene sulfonyl chloride (61.8mg, 0.3mmol), connection boric acid pinacol is added in 25mL reaction tube
Ester (114.3mg, 0.45mmol), dipotassium hydrogen phosphate (104.4mg, 2.0eq.), use ultra violet lamp reaction tube, at room temperature magnetic
Power stirring reaction 24 hours.After question response terminates, decompression boils off major part solvent, with petrol ether/ethyl acetate (20:1) for drenching
Washing lotion carries out column chromatography for separation purification to remaining mixed liquor, obtains required product, for white solid, 49.2mg, yield 70%.
Its nuclear-magnetism modal data is as follows:
1H NMR(300MHz,CDCl3) δ=7.81 (d, J=9.0Hz, 2H), 6.92 (d, J=9.0Hz, 2H), 3.83 (s,
3H),1.36(s,12H).13C NMR(75MHz,CDCl3) δ=162.2,136.5,113.3,83.5,55.0,24.9.
The synthesis of embodiment 4:4-nitrobenzene boronic acid ester
Acetonitrile 2mL, 4-toluene sulfonyl chloride (66.3mg, 0.3mmol), connection boric acid pinacol is added in 25mL reaction tube
Ester (114.3mg, 0.45mmol), dipotassium hydrogen phosphate (104.4mg, 2.0eq.), use ultra violet lamp reaction tube, at room temperature magnetic
Power stirring reaction 24 hours.After question response terminates, decompression boils off major part solvent, with petrol ether/ethyl acetate (10:1) for drenching
Washing lotion carries out column chromatography for separation purification to remaining mixed liquor, obtains required product, for yellow solid, 58.3mg, yield 78%.
Its nuclear-magnetism modal data is as follows:
1H NMR(300MHz,CDCl3) δ=8.18 (d, J=9.0Hz, 2H), 7.95 (d, J=9.0Hz, 2H), 1.36 (s,
12H).13C NMR(75MHz,CDCl3) δ=149.8,135.6,122.3,84.6,24.8.MS (EI): 249 (25), 234
(100),163(31),83(11).
Above-described embodiment is only the most preferred embodiment, every employing the inventive method or carry out routine equivalent replace
Change, modification etc. belongs to scope.
Claims (2)
1. an aromatic boronic acid ester composite synthetic method, it is characterised in that comprise the steps:
1. in reaction tube, add acetonitrile, aryl sulfonyl chloride, connection boric acid pinacol ester and dipotassium hydrogen phosphate, tighten the plug of reaction tube
Son, uses ultra violet lamp reaction tube, and at room temperature magnetic agitation is reacted 24 hours；
2., after question response terminates, decompression boils off major part solvent, with volume ratio as 10:1 ~ and the petroleum ether of 30:1 and ethyl acetate is
Leacheate carries out column chromatography for separation purification to remaining mixed liquor, obtains product.
A kind of aromatic boronic acid ester composite synthetic method the most according to claim 1, it is characterised in that: aryl sulphur in reaction
Acyl chlorides and connection boric acid pinacol ester free radical coupling.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111793080A (en) * | 2020-08-11 | 2020-10-20 | 山东卓俊实业有限公司 | Preparation method of aryl boric acid ester |
| CN111875627A (en) * | 2020-08-11 | 2020-11-03 | 山东卓俊实业有限公司 | Preparation method of aryl boric acid ester |
| CN112159422A (en) * | 2020-10-21 | 2021-01-01 | 上海应用技术大学 | Method for catalytic synthesis of phenylboronic acid ester derivative by using iridium catalyst |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111793080A (en) * | 2020-08-11 | 2020-10-20 | 山东卓俊实业有限公司 | Preparation method of aryl boric acid ester |
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| CN112159422A (en) * | 2020-10-21 | 2021-01-01 | 上海应用技术大学 | Method for catalytic synthesis of phenylboronic acid ester derivative by using iridium catalyst |
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| CN105859761B (en) | 2018-06-26 |
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Effective date of registration: 20231211 Address after: 314400, 5th Floor, Building B, North District, No. 2777 Renmin Avenue, Xucun Town, Haining City, Jiaxing City, Zhejiang Province (self declared) Patentee after: Jiaxing Platinum Electronics Co.,Ltd. Address before: 323300 Room 502, building 12, Longtan community, miaogao street, Suichang County, Lishui City, Zhejiang Province Patentee before: LISHUI SUIZHI TECHNOLOGY CONSULTATION CO.,LTD. |
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| TR01 | Transfer of patent right |