CN105820184A - Preparation method of 4-phenoxyphenylboronic acid - Google Patents
Preparation method of 4-phenoxyphenylboronic acid Download PDFInfo
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- CN105820184A CN105820184A CN201610304200.5A CN201610304200A CN105820184A CN 105820184 A CN105820184 A CN 105820184A CN 201610304200 A CN201610304200 A CN 201610304200A CN 105820184 A CN105820184 A CN 105820184A
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- phenoxy group
- phenylboric acid
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- grignard reagent
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- KFXUHRXGLWUOJT-UHFFFAOYSA-N (4-phenoxyphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OC1=CC=CC=C1 KFXUHRXGLWUOJT-UHFFFAOYSA-N 0.000 title abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 10
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 238000013517 stratification Methods 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- ZIQCCIAIROIHHR-UHFFFAOYSA-N benzene;boric acid Chemical compound OB(O)O.C1=CC=CC=C1 ZIQCCIAIROIHHR-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 229910052749 magnesium Inorganic materials 0.000 abstract description 5
- 239000011777 magnesium Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- JDUYPUMQALQRCN-UHFFFAOYSA-N 4-bromophenyl phenyl ether Chemical compound C1=CC(Br)=CC=C1OC1=CC=CC=C1 JDUYPUMQALQRCN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 8
- 238000005885 boration reaction Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 description 3
- 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004614 tumor growth 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)
Abstract
The invention discloses a preparation method of 4-phenoxyphenylboronic acid, and relates to the technical field of organic synthesis. The preparation method comprises the steps that 4-bromodiphenyl ether is taken as a raw material to react with magnesium sheets to prepare a Grignard reagent by taking tetrahydrofuran as a solvent, the obtained Grignard reagent reacts with trimethyl borate, hydrochloric acid hydrolysis is conducted to prepare coarse 4-phenoxyphenylboronic acid, and then purifying is conducted to obtain the finished 4-phenoxyphenylboronic acid. According to the preparation method, the adopted raw materials are low in cost and easy to obtain, the reaction conditions are mild, aftertreatment operation is easy, the production cost is low, the yield is high, and the method is suitable for industrialized production.
Description
Technical field:
The present invention relates to technical field of organic synthesis, be specifically related to the preparation side of a kind of 4-phenoxy group phenylboric acid
Method.
Background technology:
The character of 4-phenoxy group phenylboric acid is white powder crystal, is in a kind of purposes chemical industry widely
Mesosome, is widely used in the synthesis of medicine, dyestuff and other fine chemical products.Can in terms of medicine
To prepare anticancer class medicine, as replaced Buddhist nun according to Shandong, this medicine is a kind of oral entitled bruton's tyrosine kinase
(BTK) the pioneering new drug of inhibitor, can by with target protein Btk activity site cysteine residue
(Cys-481) optionally covalent bond, irreversibility ground suppression BTK, thus effectively stop tumor
Move to be adapted to the lymphoid tissue of tumor growth environment from B cell.4-phenoxy group phenylboric acid industrialization at present
Production have not been reported.
Summary of the invention:
The technical problem to be solved is to provide a kind of purity height, technique simple and low cost
The preparation method of 4-phenoxy group phenylboric acid.
The technical problem to be solved uses following technical scheme to realize:
A kind of preparation method of 4-phenoxy group phenylboric acid, with 4-dibromodiphenyl ether as raw material, oxolane is solvent,
First reacting with magnesium sheet and prepare Grignard reagent, gained Grignard reagent is reacted with methyl borate., then through hydrochloric acid water
Prepare 4-phenoxy group phenylboric acid crude product after solution, the most purified i.e. obtain 4-phenoxy group phenylboric acid finished product.
The preparation method of a kind of 4-phenoxy group phenylboric acid, comprises the following steps:
(1), under nitrogen protection, first magnesium sheet and oxolane are put in reaction vessel, then drip a small amount of iodine and
4-dibromodiphenyl ether cause, mixing control dropping temperature at 10～70 DEG C, then dropping residue 4-dibromodiphenyl ether with
The mixed solution of oxolane, drips complete laggard row insulation reaction, the completely rear stopped reaction of raw material reaction,
Prepare Grignard reagent；
(2) methyl borate. and oxolane mixed solution are put in reaction vessel, nitrogen protective condition
Under, be cooled to-60～-10 DEG C start to drip above-mentioned prepared Grignard reagent, drip complete, be warming up to 0～20 DEG C
Reaction, reaction terminates to add in backward reaction system the hydrochloric acid of mass concentration 10% and stirs, then stratification,
Through extraction, merge organic layer, precipitation, obtain 4-phenoxy group phenylboric acid crude product；
(3) by 4-phenoxy group phenylboric acid dissolving crude product in toluene, heated, cool down, crystallize and be centrifuged place
4-phenoxy group phenylboric acid sterling is obtained after reason.
In described step (1), 4-dibromodiphenyl ether is 1:(1.0-1.2 with the molar ratio of magnesium sheet), preferably 1:1.1.
In described step (1), dropping temperature is 20～50 DEG C, and insulation reaction temperature is 20-50 DEG C, dropping temperature
Preferably 30～35 DEG C, insulation reaction temperature is 30～35 DEG C.
In described step (2), the dropping temperature of Grignard reagent is-60～20 DEG C, preferably-40～-30 DEG C.
In described step (2), 4-dibromodiphenyl ether is 1:(1.0-1.5 with the molar ratio of methyl borate .), preferably
1:1.2。
The invention has the beneficial effects as follows: the present invention is with 4-dibromodiphenyl ether as raw material, through grignard reaction, boric acid
4-phenoxy group phenylboric acid is prepared after changing reaction and hydrolysis, raw materials used cheap and easy to get, reaction condition temperature
With, post-processing operation is simple, and production cost is relatively low, and yield is high, is suitable for industrialized production.
Detailed description of the invention:
For the technological means making the present invention realize, creation characteristic, reach purpose and effect and be readily apparent from
Solve, below in conjunction with specific embodiment, the present invention is expanded on further.
Embodiment 1
(1) Grignard reagent: first in 1000mL there-necked flask, adds 600mLTHF and 200g4-bromine two
Solution is made in phenylate stirring, standby.Then addition 25g magnesium in 2000mL there-necked flask, 20mL THF,
One granule iodine, instills the THF solution 20mL of the 4-dibromodiphenyl ether prepared, after adding thermal initiation,
At 10-20 DEG C, the THF solution of dropping residue 4-dibromodiphenyl ether, little in 30-45 DEG C of insulated and stirred 1 after dripping
Time, with liquid nitrogen reaction bulb is cooled to less than-30 DEG C standby.
(2) boration: in above-mentioned form liquid, is slowly added dropwise the 600mL THF of 110g methyl borate.
Solution, dropping process maintenance-40～-30 DEG C, stir nature and be warmed to room temperature, drip 400mL 10% after dripping off
Hydrochloric acid, refluxes 1 hour, after distilling out THF, adds 500mL cold water, stirs 30 minutes, cools down, ties
Brilliant, separation, obtains 149g4-phenoxy group phenylboric acid, and yield is 87%.
(3) purification: add the wet 4-phenoxy group phenylboric acid crude product of 149g in 1L there-necked flask, add 200mL
Toluene dissolving, precipitation, cooling down, crystallize, centrifugal to obtain 126.7g4-phenoxy group phenylboric acid product, yield is 74%.
Embodiment 2
(1) Grignard reagent: first in 1000mL there-necked flask, adds 600mLTHF and 200g4-bromine two
Solution is made in phenylate stirring, standby.Then in 2000mL there-necked flask, add 20.5g magnesium, 20mL
THF, a granule iodine, the THF solution 20mL of the 4-dibromodiphenyl ether prepared is instilled, after adding thermal initiation,
The THF solution of dropping residue 4-dibromodiphenyl ether at 10-20 DEG C, in 30-45 DEG C of insulated and stirred 1 after dripping
Hour, with liquid nitrogen reaction bulb is cooled to less than-30 DEG C standby.
(2) boration: in above-mentioned form liquid, is slowly added dropwise the 600mL THF of 91.8g methyl borate.
Solution, dropping process maintains below-30 degree, stirs nature and is warmed to room temperature, drip 400mL 10% after dripping off
Hydrochloric acid, refluxes 1 hour, after distilling out THF, adds 500mL cold water, stirs 30 minutes, cools down, ties
Brilliant, separation, obtains 145.5g4-phenoxy group phenylboric acid, and yield is 85%.
(3) purification: add the wet 4-phenoxy group phenylboric acid crude product of 145.5g in 1L there-necked flask, add 200
The dissolving of mL toluene, precipitation, cool down, crystallize, centrifugal to obtain 119.8g4-phenoxy group phenylboric acid product, yield
It is 70%.
Embodiment 3
(1) Grignard reagent: first in 1000mL there-necked flask, adds 600mLTHF and 200g4-bromine two
Solution is made in phenylate stirring, standby.Then in 2000mL there-necked flask, add 20.0g magnesium, 20mL
THF, a granule iodine, the THF solution 20mL of the 4-dibromodiphenyl ether prepared is instilled, after adding thermal initiation,
The THF solution of dropping residue 4-dibromodiphenyl ether at 45-50 DEG C, in 45-50 DEG C of insulated and stirred 1 after dripping
Hour, with liquid nitrogen reaction bulb is cooled to less than-30 DEG C standby.
(2) boration: in above-mentioned form liquid, is slowly added dropwise the 600mL THF of 91.8g methyl borate.
Solution, dropping process maintenance-50～less than-40 DEG C, stir nature and be warmed to room temperature, drip 400mL after dripping off
10% hydrochloric acid, refluxes 1 hour, after distilling out THF, add 500mL cold water, stir 30 minutes, cool down,
Crystallization, separation, obtain 150.6g4-phenoxy group phenylboric acid, and yield is 88%.
(3) purification: add the wet 4-phenoxy group phenylboric acid crude product of 150.6g in 1L there-necked flask, add 200
The dissolving of mL toluene, precipitation, cool down, crystallize, centrifugal to obtain 130.1g4-phenoxy group phenylboric acid product, yield
It is 76%.
Embodiment 4
(1) Grignard reagent: first in 1000mL there-necked flask, adds 600mLTHF and 200g4-bromine two
Solution is made in phenylate stirring, standby.Then in 2000mL there-necked flask, add 21.5g magnesium, 20mL
THF, a granule iodine, the THF solution 20mL of the 4-dibromodiphenyl ether prepared is instilled, after adding thermal initiation,
The THF solution of dropping residue 4-dibromodiphenyl ether at 30-35 DEG C, in 30-35 DEG C of insulated and stirred 1 after dripping
Hour, with liquid nitrogen reaction bulb is cooled to less than-30 DEG C standby.
(2) boration: in above-mentioned form liquid, is slowly added dropwise the 600mL THF of 100.1g methyl borate.
Solution, dropping process maintenance-40～less than-30 DEG C, stir nature and be warmed to room temperature, drip 400ml10% after dripping off
Hydrochloric acid, refluxes 1 hour, after distilling out THF, adds 500mL cold water, stirs 30 minutes, cools down, ties
Brilliant, separation, obtains 154.1g4-phenoxy group phenylboric acid, and yield is 90%.
(3) purification: add the wet 4-phenoxy group phenylboric acid crude product of 154.1g in 1L there-necked flask, add 200
The dissolving of mL toluene, precipitation, cooling down, crystallize, centrifugal to obtain 137g4-phenoxy group phenylboric acid product, yield is
80%.
The ultimate principle of the present invention and principal character and advantages of the present invention have more than been shown and described.One's own profession
Skilled person will appreciate that of industry, the present invention is not restricted to the described embodiments, above-described embodiment and explanation
The principle that the present invention is simply described described in book, without departing from the spirit and scope of the present invention,
The present invention also has various changes and modifications, and these changes and improvements both fall within claimed invention model
In enclosing.Claimed scope is defined by appending claims and equivalent thereof.
Claims (6)
1. the preparation method of a 4-phenoxy group phenylboric acid, it is characterised in that: with 4-dibromodiphenyl ether as raw material,
Oxolane is solvent, first reacts with magnesium sheet and prepares Grignard reagent, gained Grignard reagent and methyl borate.
Reaction, then after hydrochloric acid hydrolyzes, prepare 4-phenoxy group phenylboric acid crude product, the most purified i.e. obtain 4-phenoxy group benzene
Boric acid finished product.
2. the preparation method of a 4-phenoxy group phenylboric acid, it is characterised in that comprise the following steps:
(1), under nitrogen protection, first magnesium sheet and oxolane are put in reaction vessel, then drip a small amount of iodine and
4-dibromodiphenyl ether cause, mixing control dropping temperature at 10～70 DEG C, then dropping residue 4-dibromodiphenyl ether with
The mixed solution of oxolane, drips complete laggard row insulation reaction, the completely rear stopped reaction of raw material reaction,
Prepare Grignard reagent；
(2) methyl borate. and oxolane mixed solution are put in reaction vessel, nitrogen protective condition
Under, be cooled to-60～-10 DEG C start to drip above-mentioned prepared Grignard reagent, drip complete, be warming up to 0～20 DEG C
Reaction, reaction terminates to add in backward reaction system the hydrochloric acid of mass concentration 10% and stirs, then stratification,
Through extraction, merge organic layer, precipitation, obtain 4-phenoxy group phenylboric acid crude product；
(3) by 4-phenoxy group phenylboric acid dissolving crude product in toluene, heated, cool down, crystallize and be centrifuged place
4-phenoxy group phenylboric acid sterling is obtained after reason.
The preparation method of 4-phenoxy group phenylboric acid the most according to claim 1 and 2, it is characterised in that:
Described 4-dibromodiphenyl ether is 1:(1.0-1.2 with the molar ratio of magnesium sheet), preferably 1:1.1.
The preparation method of 4-phenoxy group phenylboric acid the most according to claim 2, it is characterised in that: described
4-dibromodiphenyl ether dropping temperature is 20～50 DEG C, and insulation reaction temperature is 20-50 DEG C, and dropping temperature is preferred
30～35 DEG C, insulation reaction temperature is 30～35 DEG C.
The preparation method of 4-phenoxy group phenylboric acid the most according to claim 2, it is characterised in that: described
The dropping temperature of Grignard reagent is-60～20 DEG C, preferably-40～-30 DEG C.
The preparation method of 4-phenoxy group phenylboric acid the most according to claim 2, it is characterised in that: described
4-dibromodiphenyl ether is 1:(1.0-1.5 with the molar ratio of methyl borate .), preferably 1:1.2.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106589184A (en) * | 2016-12-30 | 2017-04-26 | 中国石油大学(华东) | High polymer with trace water detection property and preparation method and application thereof |
| CN110669064A (en) * | 2018-07-03 | 2020-01-10 | 华东师范大学 | Preparation method of arylboronic acid |
| CN110964048A (en) * | 2019-12-18 | 2020-04-07 | 江苏创拓新材料有限公司 | Method for recycling organic boric acid waste liquid |
| CN111072697A (en) * | 2019-12-28 | 2020-04-28 | 沧州普瑞东方科技有限公司 | Preparation method of 4-phenoxyphenylboronic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106589184A (en) * | 2016-12-30 | 2017-04-26 | 中国石油大学(华东) | High polymer with trace water detection property and preparation method and application thereof |
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| CN110669064A (en) * | 2018-07-03 | 2020-01-10 | 华东师范大学 | Preparation method of arylboronic acid |
| CN110964048A (en) * | 2019-12-18 | 2020-04-07 | 江苏创拓新材料有限公司 | Method for recycling organic boric acid waste liquid |
| CN110964048B (en) * | 2019-12-18 | 2022-05-03 | 江苏创拓新材料有限公司 | Method for recycling organic boric acid waste liquid |
| CN111072697A (en) * | 2019-12-28 | 2020-04-28 | 沧州普瑞东方科技有限公司 | Preparation method of 4-phenoxyphenylboronic acid |
| CN111072697B (en) * | 2019-12-28 | 2022-05-20 | 沧州普瑞东方科技有限公司 | Preparation method of 4-phenoxyphenylboronic acid |
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Application publication date: 20160803 |