CN105949040A - Preparation method of 2, 3-difluoro-4-alkoxy phenol - Google Patents
Preparation method of 2, 3-difluoro-4-alkoxy phenol Download PDFInfo
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- CN105949040A CN105949040A CN201610300888.XA CN201610300888A CN105949040A CN 105949040 A CN105949040 A CN 105949040A CN 201610300888 A CN201610300888 A CN 201610300888A CN 105949040 A CN105949040 A CN 105949040A
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- fluoro
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- alkoxy phenol
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000005885 boration reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 238000006138 lithiation reaction Methods 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004327 boric acid Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 claims description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 6
- UKTDQTGMXUHPIF-UHFFFAOYSA-N [Na].S(O)(O)=O Chemical compound [Na].S(O)(O)=O UKTDQTGMXUHPIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000001914 filtration Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 abstract 1
- 238000004537 pulping 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
- 239000000047 product Substances 0.000 description 11
- 238000001514 detection method Methods 0.000 description 8
- 238000005070 sampling Methods 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000012805 post-processing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
Relating to the technical field of organic synthesis, the invention discloses a preparation method of 2, 3-difluoro-4-alkoxy phenol. 2, 3-difluorobenzene ether, n-butyllithium, trimethyl borate, acetic acid and hydrogen peroxide are adopted as the raw materials, tetrahydrofuran is taken as the solvent, and by means of organic lithiation, boration, oxidization, pulping filtration and other steps, a 2, 3-difluoro-4-alkoxy phenol product can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple aftertreatment operation, low production cost, a total yield up to more than 66%, and product purity of more than 99.9%, and is suitable for industrialized production.
Description
Technical field:
The present invention relates to technical field of organic synthesis, be specifically related to a kind of 2, the system of 3-bis-fluoro-4-alkoxy phenol
Preparation Method.
Background technology:
The character of 2,3-bis-fluoro-4-alkoxy phenols is white or off-white powder shape crystal, is that a kind of purposes is non-
Chemical intermediate the most widely, is widely used in the synthesis of medicine, pesticide and other fine chemical products.
Through retrieval, the shortcomings such as existing process costs is high, danger coefficient is big.
Summary of the invention:
The technical problem to be solved be to provide a kind of low cost, yield are high, operation is simple and
The preparation method of environment amenable 2,3-bis-fluoro-4-alkoxy phenol.
The technical problem to be solved uses following technical scheme to realize:
A kind of 2, the preparation method of 3-bis-fluoro-4-alkoxy phenol, comprise the following steps:
(1) 4-alkoxyl-2, the preparation of 3-difluorobenzene boric acid: by 2,3-difluoro phenylate adds in cryogenic equipment, with
Oxolane, as solvent, then drips n-BuLi, and lithiation drips methyl borate. after terminating,
Boration reaction sloughs solvent, rejection filter after terminating, and obtains 4-alkoxyl-2,3-difluorobenzene boric acid；
The preparation of (2) 2,3-bis-fluoro-4-alkoxy phenol: by 4-alkoxyl-2,3-difluorobenzene boric acid adds in still,
With oxolane and acetic acid as solvent, dropping hydrogen peroxide carries out oxidation reaction, reaction terminate after through sulfurous acid
Sodium processes, and sloughs solvent, and add water rejection filter, obtains product 2,3-bis-fluoro-4-alkoxy phenol.
Concrete synthetic route is as follows:
Described butyl lithium and 2, the molar ratio of 3-difluoro phenylate is 2.8～3.2, preferably 3.0.
The dropping temperature of described butyl lithium is-78～-85 DEG C, preferably-80～-83 DEG C.
The dropping temperature of described methyl borate. is-75～-85 DEG C, preferably-78～-83 DEG C.
The dropping temperature of described hydrogen peroxide is 15～30 DEG C, preferably 20～25 DEG C.
Described acetic acid and 2, the molar ratio of 3-difluoro phenylate is 3.5～4.5, preferably 4.0.
The invention has the beneficial effects as follows: the cheaper starting materials that the present invention uses is easy to get, and reaction condition is the gentleest,
Post-processing operation is simple, and production cost is relatively low, and total recovery reaches more than 66%, and product purity reaches 99.9%
Above, it 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) in 1L low-temperature (low temperature) vessel, add 2.3-difluoro ether 83.3g and 500.0g THF, fed intake
Journey nitrogen gas shielded, opens cooling, is cooled between-78～85 DEG C, starts to drip n-BuLi 168.0g, add
It is incubated 2h, middle control between complete-78～85 DEG C, remains 15.5%, start to drip methyl borate. 84.0g, temperature
Degree controls between-75～85 DEG C, after dripping insulated and stirred 1h, and sampling detection, remain 2.5%, heat up
Post processing, adds 100.0g water in container, and after sloughing THF, to obtain 2.3-bis-fluoro-4-ethoxybenzene boric acid thick for sucking filtration
Product 110.0g, HPLC purity 98.5%；
(2) in tetra-mouthfuls of reaction vessels of 1L, 326.7g oxolane and 132.9g glacial acetic acid, stirring are added
30min, add 110.0g 2.3-bis-fluoro-4-ethoxybenzene crude boronic acid, stir half an hour, control temperature 15～
Between 25 DEG C, dripping 111.1g hydrogen peroxide, drip complete insulated and stirred 1h, sampling detection, raw material remains
0.15%, add water in container 200.0g and 15.1g sodium sulfite treatment, and layering, upper organic phase gets rid of rate
2.3-bis-fluoro-4-thanatol crude product 85.0g, distill to obtain product 64.8g, GC purity: 99.96%,
Two step yields 69.8%.
Embodiment 2
(1) in 1L low-temperature (low temperature) vessel, add 2.3-difluoro ether 83.3g and 500.0gTHF, fed intake
Journey nitrogen gas shielded, opens cooling, is cooled between-78～85 DEG C, starts to drip n-BuLi 155.0g, add
It is incubated 2h, middle control between complete-78～85 DEG C, remains 21.5%, start to drip methyl borate. 84.0g, temperature
Degree controls between-75～85 DEG C, after dripping insulated and stirred 1h, and sampling detection, remain 2.8%, heat up
Post processing, adds 100.0g water in container, and after sloughing THF, to obtain 2.3-bis-fluoro-4-ethoxybenzene boric acid thick for sucking filtration
Product 103.0g, HPLC purity 96.7%；
(2) in tetra-mouthfuls of reaction vessels of 1L, 326.7g oxolane and 132.9g glacial acetic acid, stirring are added
30min, add 103.0g 2.3-bis-fluoro-4-ethoxybenzene crude boronic acid, stir 30min, control temperature 15～
Between 25 DEG C, dripping 111.1g hydrogen peroxide, drip complete insulated and stirred 1h, sampling detection, raw material remains
0.10%, add water in container 200.0g and 15.1g sodium sulfite treatment, and layering, upper organic phase gets rid of rate
2.3-bis-fluoro-4-thanatol crude product 79.5g, distill to obtain product 62.2g, GC purity: 99.92%,
Two step yields 67.9%.
Embodiment 3
(1) in 1L low-temperature (low temperature) vessel, add 2.3-difluoro ether 83.3g and 500.0g THF, fed intake
Journey nitrogen gas shielded, opens cooling, is cooled between-78～85 DEG C, starts to drip n-BuLi 168.0g, add
It is incubated 2h, middle control between complete-78～85 DEG C, remains 20.5%, start to drip methyl borate. 80.0g, temperature
Degree controls between-75～85 DEG C, after dripping insulated and stirred 1h, and sampling detection, remain 3.2%, heat up
Post processing, adds 100.0g water in container, and after sloughing THF, to obtain 2.3-bis-fluoro-4-ethoxybenzene boric acid thick for sucking filtration
Product 100.2g, HPLC purity 96.5%；
(2) in tetra-mouthfuls of reaction vessels of 1L, 326.7g oxolane and 132.9g glacial acetic acid, stirring are added
Half an hour, add 100.2g 2.3-bis-fluoro-4-ethoxybenzene crude boronic acid, stir 30min, control temperature 15～
Between 25 DEG C, dripping 111.1g hydrogen peroxide, drip complete insulated and stirred 1h, sampling detection, raw material remains
0.22%, add water in container 200.0g and 15.1g sodium sulfite treatment, and layering, upper organic phase gets rid of rate
2.3-bis-fluoro-4-thanatol crude product 76.0g, distill to obtain product 61.1g, GC purity: 99.95%,
Two step yields 66.0%.
Embodiment 4
(1) in 1L low-temperature (low temperature) vessel, add 2.3-difluoro ether 83.3g and 500.0gTHF, fed intake
Journey nitrogen gas shielded, opens cooling, is cooled between-78～85 DEG C, starts to drip n-BuLi 168.0g, add
It is incubated 2h, middle control between complete-78～85 DEG C, remains 15.5%, start to drip methyl borate. 84.0g, temperature
Degree controls between-75～85 DEG C, after dripping insulated and stirred 1h, and sampling detection, remain 2.5%, heat up
Post processing, adds 100.0g water in container, and after sloughing THF, to obtain 2.3-bis-fluoro-4-ethoxybenzene boric acid thick for sucking filtration
Product 110.0g, HPLC purity 97.4%；
(2) in tetra-mouthfuls of reaction vessels of 1L, 326.7g oxolane and 132.9g glacial acetic acid, stirring are added
30min, add 110.0g 2.3-bis-fluoro-4-ethoxybenzene crude boronic acid, stir 30min, control temperature 15～
Between 25 DEG C, dripping 100.0g hydrogen peroxide, drip complete insulated and stirred 1h, sampling detection, raw material remains
0.44%, add water in container 200.0g and 15.1g sodium sulfite treatment, and layering, upper organic phase gets rid of rate
2.3-bis-fluoro-4-thanatol crude product 80.5g, distill to obtain product 62.8g, GC purity: 99.96%,
Two step yields 67.9%.
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 (7)
1. one kind 2, the preparation method of 3-bis-fluoro-4-alkoxy phenol, it is characterised in that: with 2,3-difluoro phenylate,
N-BuLi, methyl borate., acetic acid and hydrogen peroxide are raw material, and oxolane is solvent, through organolithium
Change, boration, aoxidize, the steps such as purification of pulling an oar obtain 2,3-bis-fluoro-4-alkoxy benzene phenolic product.
2. one kind 2, the preparation method of 3-bis-fluoro-4-alkoxy phenol, it is characterised in that comprise the following steps:
(1) 4-alkoxyl-2, the preparation of 3-difluorobenzene boric acid: by 2,3-difluoro phenylate adds in cryogenic equipment, with
Oxolane, as solvent, then drips n-BuLi, and lithiation drips methyl borate. after terminating,
Boration reaction sloughs solvent, rejection filter after terminating, and obtains 4-alkoxyl-2,3-difluorobenzene boric acid；
The preparation of (2) 2,3-bis-fluoro-4-alkoxy phenol: by 4-alkoxyl-2,3-difluorobenzene boric acid adds in still,
With oxolane and acetic acid as solvent, dropping hydrogen peroxide carries out oxidation reaction, reaction terminate after through sulfurous acid
Sodium processes, and sloughs solvent, and add water rejection filter, obtains product 2,3-bis-fluoro-4-alkoxy phenol.
The preparation method of the most according to claim 1 and 22,3-bis-fluoro-4-alkoxy phenol, its feature
Being: described butyl lithium and 2, the molar ratio of 3-difluoro phenylate is 2.8～3.2, preferably 3.0.
The preparation method of the most according to claim 1 and 22,3-bis-fluoro-4-alkoxy phenol, its feature
It is: the dropping temperature of described butyl lithium is-78～-85 DEG C, preferably-80～-83 DEG C.
The preparation method of the most according to claim 1 and 22,3-bis-fluoro-4-alkoxy phenol, its feature
It is: the dropping temperature of described methyl borate. is-75～-85 DEG C, preferably-78～-83 DEG C.
The preparation method of the most according to claim 1 and 22,3-bis-fluoro-4-alkoxy phenol, its feature
It is: the dropping temperature of described hydrogen peroxide is 15～30 DEG C, preferably 20～25 DEG C.
The preparation method of the most according to claim 1 and 22,3-bis-fluoro-4-alkoxy phenol, its feature
Being: described acetic acid and 2, the molar ratio of 3-difluoro phenylate is 3.5～4.5, preferably 4.0.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610300888.XA CN105949040A (en) | 2016-05-06 | 2016-05-06 | Preparation method of 2, 3-difluoro-4-alkoxy phenol |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610300888.XA CN105949040A (en) | 2016-05-06 | 2016-05-06 | Preparation method of 2, 3-difluoro-4-alkoxy phenol |
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| CN201610300888.XA Pending CN105949040A (en) | 2016-05-06 | 2016-05-06 | Preparation method of 2, 3-difluoro-4-alkoxy phenol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110922306A (en) * | 2019-12-17 | 2020-03-27 | 蚌埠中实化学技术有限公司 | Synthesis process of 2, 3-difluoro-4-alkoxy phenol |
| CN113930120A (en) * | 2021-11-29 | 2022-01-14 | 河南蓝翎环科防水材料有限公司 | High-strength explosion-proof protective coating and production process thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011026274A (en) * | 2009-07-29 | 2011-02-10 | Dic Corp | Difluorobenzene derivative, liquid crystal composition containing the compound and liquid crystal display element |
| CN103030534A (en) * | 2012-11-23 | 2013-04-10 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal compound containing 2,3-difluorophenyl group, and preparation method and application thereof |
| CN104479687A (en) * | 2014-12-17 | 2015-04-01 | 石家庄诚志永华显示材料有限公司 | Cycloheptyl-2,3-difluorophenyl negative liquid crystal compound, and preparation method and application thereof |
-
2016
- 2016-05-06 CN CN201610300888.XA patent/CN105949040A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011026274A (en) * | 2009-07-29 | 2011-02-10 | Dic Corp | Difluorobenzene derivative, liquid crystal composition containing the compound and liquid crystal display element |
| CN103030534A (en) * | 2012-11-23 | 2013-04-10 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal compound containing 2,3-difluorophenyl group, and preparation method and application thereof |
| CN104479687A (en) * | 2014-12-17 | 2015-04-01 | 石家庄诚志永华显示材料有限公司 | Cycloheptyl-2,3-difluorophenyl negative liquid crystal compound, and preparation method and application thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110922306A (en) * | 2019-12-17 | 2020-03-27 | 蚌埠中实化学技术有限公司 | Synthesis process of 2, 3-difluoro-4-alkoxy phenol |
| CN110922306B (en) * | 2019-12-17 | 2023-09-29 | 蚌埠中实化学技术有限公司 | Synthesis process of 2, 3-difluoro-4-alkoxyl phenol |
| CN113930120A (en) * | 2021-11-29 | 2022-01-14 | 河南蓝翎环科防水材料有限公司 | High-strength explosion-proof protective coating and production process thereof |
| CN113930120B (en) * | 2021-11-29 | 2022-05-13 | 河南蓝翎环科防水材料有限公司 | High-strength explosion-proof protective coating and production process thereof |
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Application publication date: 20160921 |