CN111234843A - Preparation method of alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer - Google Patents
Preparation method of alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer Download PDFInfo
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Abstract
The invention relates to the field of liquid crystal display, in particular to a preparation method of alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer for liquid crystal display, which has the following structural general formula:
Description
Technical Field
The invention relates to the field of liquid crystal display, in particular to a preparation method of an alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer for liquid crystal display.
Background
The development of new liquid crystal compounds and compositions comprising the same are extremely important for improving various properties of liquid crystals and improving the application effects of liquid crystal displays. During the preparation of the mixed liquid crystal composition, some single crystal compounds with a certain special performance are often added, the optical anisotropy is an important property of the liquid crystal material, people pursue the liquid crystal display with high response speed, wide viewing angle and the like, and the synthesis of the optical anisotropy liquid crystal material is concerned by people; in addition, liquid crystal materials with low melting point, low viscosity and strong stability are rare, single crystal compounds with special properties are expected by researchers, and the 1-alkoxy-2, 3-difluoro-4- (trans-4-alkylcyclohexyl (phenylethynyl)) benzene liquid crystal monomer has the advantages of low melting point, low viscosity, high response speed, high birefringence and the like, and meanwhile, the liquid crystal monomer has large negative dielectric anisotropy and good stability, and the liquid crystal monomer has wide application range due to the excellent properties and can be used as a base material for forming a liquid crystal medium, so that the synthesis of the compound has important application value. At present, in the prior art, the alkoxy difluorophenylacetylene raw material is not easy to obtain, the preparation process is complex, the cost is high, and alkoxy difluorophenylacetylene self-coupling impurities are easy to generate in the coupling process of the sonogashira, and are difficult to remove, so that the purity of the final product is poor, and the yield is low.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a novel method for preparing alkoxy difluoro (trans-4-alkyl cyclohexyl) phenylethynyl benzene liquid crystal monomer, and the preparation method provided by the invention has the advantages of easily available raw materials, stable process, high product purity and low production cost, and is beneficial to realizing large-scale production.
The technical scheme for solving the technical problems is as follows:
a preparation method of alkoxy difluoro (trans-4-alkyl cyclohexyl) phenylethynyl benzene liquid crystal monomer comprises the following steps:
adding organic base into trans-4-alkylcyclohexyl substituted bromobenzene in a mass ratio of 1 (3-5) to the trans-4-alkylcyclohexyl substituted bromobenzene under the protection of inert gas, uniformly mixing, adding palladium catalyst, copper catalyst and base, heating to 70-90 ℃, dropwise adding 2-methyl-3-butyne-2-ol in a mass ratio of 1: (2-4) preparing a mixed solution by using organic base, keeping the temperature for 5-10 hours after dropwise adding, performing acid hydrolysis, removing a solvent, and recrystallizing to obtain an intermediate I, wherein the reaction equation is as follows:
wherein R is1Is straight-chain saturated alkane with 3-5 carbon atoms;
and (2) removing acetone from the intermediate I under the action of strong alkali to obtain an intermediate II, wherein the reaction equation is as follows:
step (3), adding organic base into 1-bromo-4-alkoxy-2, 3-difluorobenzene in a mass ratio of 1 (3-5) to the 1-bromo-4-alkoxy-2, 3-difluorobenzene, uniformly mixing, adding a palladium catalyst, a copper catalyst, alkali and an inert gas for replacement, heating to 70-90 ℃, and dropwise adding an intermediate II in a mass ratio of 1: (2-4), after dropwise adding, reacting for 3-5 hours under a heat preservation condition, decompressing to remove the organic base, extracting, removing the solvent, and recrystallizing to obtain the alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer, wherein the reaction equation is as follows:
wherein R is2Is a saturated straight-chain alkane having 2 to 5 carbon atoms.
On the basis of the technical scheme, the invention can be further improved as follows,
further, in the step (1) and the step (3), the organic base is any one or more of triethylamine or diisopropylamine.
Further, in the step (1) and the step (3), the palladium catalyst is any one or more of bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium and 1,1' -bis (diphenylphosphino) ferrocene palladium dichloride (II); the copper catalyst is any one or more of copper chloride, cuprous iodide and copper iodide, and the alkali is any one or more of potassium carbonate and potassium hydroxide.
Further, in the step (2), the strong base is any one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide or potassium tert-butoxide.
The invention has the following beneficial effects:
(1) the synthesis method has the innovation points that one or more of sodium hydroxide, potassium tert-butoxide or sodium tert-amylate is adopted to replace dangerous reagents such as sodium hydride and the like which are used originally, so that fewer byproducts are produced, the yield is high, and the method is favorable for industrial production;
(2) 1-bromo-4-alkoxy-2, 3-difluorobenzene is innovatively used for replacing the traditional 1-iodo-4-alkoxy-2, 3-difluorobenzene as a raw material and is subjected to coupling reaction with the intermediate II to prepare the final liquid crystal compound, so that the cost of the raw material is low, the raw material is easy to obtain, and the industrialization is facilitated.
(3) Compared with the self-coupling impurities generated by 2, 3-difluoro-4-alkoxy phenylacetylene, the self-coupling impurities generated by the intermediate II are easier to remove, the high-purity liquid crystal monomer is easier to obtain, and the yield is higher.
Detailed Description
Exemplary embodiments that embody features and advantages of the invention are described in detail below. It is to be understood that the invention is capable of other and different embodiments and its several details are capable of modification without departing from the scope of the invention, and that the description is intended to be illustrative in nature and not to be construed as limiting the invention.
Example 1
When R is1Is n-propyl, R2In the case of ethyl, the liquid crystal monomer of alkoxydifluoro (trans-4-alkylcyclohexyl) phenylethynylbenzene to be prepared is 1-ethoxy-2, 3-difluoro-4- (trans-4-n-propylcyclohexyl (phenylethynyl)) benzene, the structural formula is shown as follows, and the corresponding intermediates are intermediate I a and intermediate IIa respectively.
The preparation method comprises the following steps:
1) 21.1g (0.075mol) of trans-4-n-propylcyclohexylbromobenzene, 45.0g of triethylamine, 0.3g of bistriphenylphosphine palladium dichloride, 0.2g of cuprous iodide and 1.0g of DMAP were added dropwise to a 250ml three-necked flask under nitrogen protection, and a mixture of 9.8g of 2-methyl-3-butyn-2-ol and 20.0g of triethylamine was added dropwise. Heating to 70-90 ℃, and carrying out heat preservation and reflux for 6 hours. After the hydrolysis is finished, the temperature is reduced, dilute hydrochloric acid is added for hydrolysis, toluene extraction is carried out, water washing is carried out until the mixture is neutral, recrystallization is carried out after the solvent is removed, and the yellow solid intermediate Ia19.4g, the purity is 99.3 percent and the yield is 91 percent, is obtained after drying.
2) 16.0g (0.056mol) of the intermediate Ia, 0.7g of potassium tert-butoxide, 90.0g of toluene and 20g of tetrahydrofuran are added into a 250ml three-necked flask, and the mixture is heated to 80-90 ℃ and refluxed for 1 hour. After hydrolysis, the organic phase was washed with water to neutral, and after the solvent was removed under reduced pressure, recrystallization was carried out to obtain 11.5g of intermediate IIa as a white solid, purity was 99%, and yield was 91%.
3) Under the protection of nitrogen, 23.7g (0.1mol) of 4-ethoxy-2, 3-difluorobromobenzene, 38g of triethylamine, 0.21g of bis (triphenylphosphine) palladium dichloride, 0.06g of cuprous iodide and 0.4g of triphenylphosphine are added into a 250ml three-necked bottle, the temperature is increased to 70-80 ℃, 15.6g (0.11mol) of prepared intermediate IIa and 38g of triethylamine solution are dropwise added into the bottle, the temperature is kept for 3 hours after the dropwise addition, after the temperature is kept, 156.4g of concentrated hydrochloric acid and 312.8g of water are poured into the bottle for hydrolysis, toluene is added for extraction, layering is carried out, after the solution is washed to be neutral, anhydrous sodium sulfate is dried, a dry solvent is removed, the solution is recrystallized twice by toluene/anhydrous ethanol, and the product a is dried to obtain 28.2g, the GC purity is 99.96%, and the yield is 94.0%.
1-ethoxy-2, 3-difluoro-4- (trans-4-n-propylcyclohexyl (phenylethynyl)) benzene:1H NMR(400MHz,CDCl3)；δ：7.43-7.45(m，2H)；7.13-7.17(m，3H)；6.64-6.68(m，1H)；4.07-4.13(q，2H)；2.72(m,1H)；1.32-1.62(m,16H)；0.91-0.95(t，3H)；13C NMR(400MHz,CDCl3)；δ:152.91,152.81,150.41,150.31,148.82,148.80,148.74,148.72,143.53,142.63,142.50，140.17,140.03,131.51,128.57,127.04,120.03，109.03，109.01，105.83，105.70，94.02，93.99，81.14，81.10，65.37，38.00，31.10，30.95，24.36，14.65，13.76；MS,m/z 382(M+)
example 2
When R1 is n-pentyl and R2 is ethyl, the product to be prepared is 1-ethoxy-2, 3-difluoro-4- (trans-4-n-pentylcyclohexyl (phenylethynyl)) benzene, of the formula shown below, the corresponding intermediates being intermediate I b and intermediate iib, respectively.
The preparation method comprises the following steps:
1) under nitrogen protection, 23.1g (0.075mol) of trans-4-n-pentylcyclohexylbromobenzene, 45.0g of triethylamine, 0.3g of bistriphenylphosphine palladium dichloride, 0.2g of cuprous iodide and 1.0g of DMAP were added dropwise to a 250ml three-necked flask, and a mixture of 9.8g of 2-methyl-3-butyn-2-ol and 20.0g of triethylamine was added dropwise. Heating to 70-90 ℃, and carrying out heat preservation and reflux for 6 hours. After the hydrolysis is finished, the temperature is reduced, dilute hydrochloric acid is added for hydrolysis, toluene extraction is carried out, water washing is carried out until the mixture is neutral, recrystallization is carried out after the solvent is removed, and the yellow solid intermediate Ib21.2g is obtained after drying, the purity is 99.1 percent, and the yield is 90 percent.
2) A250 ml three-necked flask was charged with 18.4g (0.059mol) of intermediate Ib, 0.7g of potassium tert-butoxide, 90.0g of toluene and 20g of tetrahydrofuran, and heated to 80-90 ℃ under reflux for 1 hour. After hydrolysis, the organic phase is washed to neutrality by water, and after the solvent is removed under reduced pressure, recrystallization is carried out, and drying is carried out to obtain 13.4g of white solid intermediate IIb, the purity is 99.2 percent, and the yield is 89 percent.
3) Under the protection of nitrogen, 23.7g (0.1mol) of 4-ethoxy-2, 3-difluorobromobenzene, 38g of triethylamine, 0.21g of bis (triphenylphosphine) palladium dichloride, 0.06g of cuprous iodide and 0.4g of triphenylphosphine are added into a 250ml three-necked bottle, the temperature is increased to 70-80 ℃, 28.0g (0.11mol) of prepared intermediate IIb and 45g of triethylamine solution are dropwise added into the bottle, after the dropwise addition is finished and the temperature is kept for 3 hours, after the temperature is kept, 156.4g of concentrated hydrochloric acid and 312.8g of water are poured into the bottle for hydrolysis, toluene is added for extraction, layering is carried out, after the bottle is washed to be neutral, anhydrous sodium sulfate is dried, a dry solvent is removed, the product b is recrystallized twice by toluene/anhydrous ethanol, and after drying, the product b has 39.0g of GC purity and the yield is 95.0%.
1-ethoxy-2, 3-difluoro-4- (trans-4-n-pentylcyclohexyl (phenylethynyl)) benzene:1H NMR(400MHz,CDCl3)；δ：7.42-7.45(m，2H)；7.13-7.18(m，3H)；6.64-6.69(m，1H)；4.08-4.13(q，2H)；2.72(m,1H)；1.29-1.62(m,20H)；0.87-0.90(t，3H)；13C NMR(400MHz,CDCl3)；δ:152.92,152.81,150.42,150.31,148.82,148.79,148.73,148.71,143.80,142.64,142.50,140.18,140.04,131.52,128.50,127.06,127.03,119.99，109.04，109.01，105.85，105.72，84.03，93.99，81.12，81.08，65.37，35.92，31.47，31.10，30.95，22.55，14.66，14.04；MS,m/z 410(M+)
the above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A preparation method of an alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer is characterized by comprising the following steps:
adding organic base into trans-4-alkylcyclohexyl substituted bromobenzene in a mass ratio of 1 (3-5) to the trans-4-alkylcyclohexyl substituted bromobenzene under the protection of inert gas, uniformly mixing, adding palladium catalyst, copper catalyst and base, heating to 70-90 ℃, dropwise adding 2-methyl-3-butyne-2-ol in a mass ratio of 1: (2-4) preparing a mixed solution by using organic base, keeping the temperature for 5-10 hours after dropwise adding, performing acid hydrolysis, removing a solvent, and recrystallizing to obtain an intermediate I, wherein the reaction equation is as follows:
wherein R is1Is straight-chain saturated alkane with 3-5 carbon atoms;
and (2) removing acetone from the intermediate I under the action of strong alkali to obtain an intermediate II, wherein the reaction equation is as follows:
step (3), adding organic base into 1-bromo-4-alkoxy-2, 3-difluorobenzene in a mass ratio of 1 (3-5) to the 1-bromo-4-alkoxy-2, 3-difluorobenzene, uniformly mixing, adding a palladium catalyst, a copper catalyst, alkali and an inert gas for replacement, heating to 70-90 ℃, and dropwise adding an intermediate II in a mass ratio of 1: (2-4), after dropwise adding, reacting for 3-5 hours under a heat preservation condition, decompressing to remove the organic base, extracting, removing the solvent, and recrystallizing to obtain the alkoxy difluoro (trans-4-alkylcyclohexyl) phenylethynyl benzene liquid crystal monomer, wherein the reaction equation is as follows:
wherein R is2Is a saturated straight-chain alkane having 2 to 5 carbon atoms.
2. The preparation method according to claim 1, wherein in the step (1) and the step (3), the organic base is any one or more of triethylamine or diisopropylamine.
3. The preparation method according to claim 1, wherein in the step (1) and the step (3), the palladium catalyst is any one or more of bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, and 1,1' -bis (diphenylphosphino) ferrocene palladium dichloride (II); the copper catalyst is any one or more of copper chloride, cuprous iodide and copper iodide, and the alkali is any one or more of potassium carbonate and potassium hydroxide.
4. The preparation method according to claim 1, wherein in the step (2), the strong base is any one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide or potassium tert-butoxide.
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Application publication date: 20200605 |