CN102675062A - Method for preparing difluoromethoxy bridge type liquid crystal - Google Patents
Method for preparing difluoromethoxy bridge type liquid crystal Download PDFInfo
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Abstract
The invention discloses a method for preparing a difluoromethoxy bridge type liquid crystal compound, which comprises the following steps: uniformly mixing a compound shown in a formula II and a compound shown in a formula III with alkali under the condition that a catalyst exists for reaction and obtaining a compound shown in a formula I after reaction. The method has the beneficial effects that a reaction substrate is changed into the compound shown in the formula II and a phenylo boric acid derivative shown in the formula III, the reaction steps are reduced, a reaction intermediate is simplified, the total reaction yield is greatly improved, and different group compounds can use the same intermediate formula I. The method is particularly suitable for preparing the difluoromethoxy bridge type liquid crystal compound. Formula II, formula III and formula I are shown in the instruction.
Description
Technical field
The invention belongs to the synthesis technical field of monomer liquid crystal in the electronic material, relate to the method that a kind of preparation contains the monomer liquid crystal of difluoro methoxy bridge.
Background technology
Along with developing rapidly of lcd technology, TFT-LCD has been called the main flow of liquid-crystal display, but problems such as the animation ghost in the video, hangover still do not solve, and the major cause that causes this phenomenon is that liquid crystal response speed is slow.The viscosity of liquid crystal material has directly determined the response speed of liquid-crystal display.Traditional ester liquid crystal, the liquid crystal of cyano-containing are restricted in the TFT lcd applications because resistivity is lower, voltage retention is low.A large amount of researchs show that fluorinated liquid crystal is the material of the present the most suitable TFT liquid-crystal display of being found.Difluoromethyl ethers liquid crystal has been the fluorine liquid crystal of exploitation gradually since phase late 1980s; Receive extensive attention in recent years, especially after the liquid crystal molecule skeleton is introduced the difluoro methyl ether bridged bond, can have moderate optical anisotropy (Δ n) value; Improve dielectric anisotropy (Δ ε) value; Reduce rotary viscosity (γ) value of molecule, improve the intermiscibility and the low-temperature performance of liquid crystal, over-all properties is very excellent.
Introducing the difluoro methyl ether bridged bond at the liquid crystal molecule skeleton has several different methods, and multiple telling about arranged in different documents.
USP 6231785 has introduced and has carried out the bromo-lithium exchange reactions with difluorodibromomethane and lithium aryl and obtain 1-bromo-1, and 1-difluoromethyl benzene derivative generates difluoro methoxy bridge class liquid crystalline cpd with the reaction of trifluoromethyl phenol sodium again.
USP 6787062 has introduced and has used 1, and 3-dimercaptopropane, trifluoromethane sulfonic acid become sulfonium salt with organic acid, again with amphyl, bromine, hydrogen fluoride triethylamine salt reaction generation difluoro methoxy bridge class liquid crystalline cpd.
Through experimental verification; These two kinds of methods are owing to the molecular structure that will from left to right carry out compound successively is synthetic, so total recovery is all very low, the compound total recovery of using two kinds of methods to obtain all has only 20%; And the conversion end alkyl will synthesize again, be unfavorable for comprehensively reducing cost.
Summary of the invention
The purpose of this invention is to provide the method that a kind of preparation contains difluoro methoxy bridge class liquid crystal.
The method for preparing compound shown in the formula I provided by the invention comprises the steps: under the condition that catalyzer exists, compound shown in compound shown in the formula II and the formula III and alkali mixing to be reacted, and reaction finishes and obtains compound shown in the said formula I;
Formula II
Formula III
Formula I
In the said formula II-formula III, R all is selected from least a in the alkenyl of alkoxyl group and C2-C8 of straight chained alkyl, C1-C8 of C1-C8, and X is Br or I;
A
1, A
2And A
3All be selected from singly-bound, phenyl, fluorine substituted benzene cyclic group, pyrimidyl, pyridyl, dioxane base, at least a in THP trtrahydropyranyl and the octahydro pentalene base;
Y
1And Y
2All be selected among H and the F any one.
The reaction formula of aforesaid method is as follows:
Reaction expression is as follows:
In the aforesaid method, said catalyzer is that four triphenyl phosphorus close palladium;
Said alkali is selected from least a in yellow soda ash, sodium hydrogencarbonate, salt of wormwood, potassiumphosphate and the sodium hydroxide, preferred yellow soda ash.
Compound shown in the said formula II is 1: 0.001～0.1 with the mole dosage ratio that feeds intake of said catalyzer, preferred 1: 0.01;
Said alkali is 1～5: 1 with the mole dosage ratio that feeds intake of compound shown in the said formula III, preferred 2.5: 1;
Compound shown in the said formula II is 1 with the mole dosage ratio that feeds intake of compound shown in the formula III: 0.8-1.5, preferred 1: 1.1.
Said being reflected in the solvent carried out.
Said solvent is selected from THF, ethanol, water, N, N N, N, and at least a in N N,N-DIMETHYLACETAMIDE, toluene and the benzene is to mix the mixture that gets at 2: 1: 1 by toluene, second alcohol and water with volume ratio preferably;
The amount ratio of compound is 1L: 0.5-4mol shown in said solvent and the said formula II, preferred 1L: 2mol.
In the said reactions step, temperature is 70-150 ℃, and preferred 90 ℃, the time is 4-10 hour, preferred 6 hours.
Preparation provided by the invention contains the method for difluoro methoxy bridge class liquid crystalline cpd; Than additive method, the present invention becomes phenylo boric acid verivate shown in compound shown in the formula II and the formula III with reaction substrate, has reduced reactions step; Simplify reaction intermediate; Overall yield of reaction significantly improves, and different group compounds all can use compound shown in the same midbody formula II, is suitable for preparing difluoro methoxy bridge class liquid crystalline cpd especially.
Embodiment
Below in conjunction with specific embodiment the present invention is done further elaboration, but the present invention is not limited to following examples.Said method is ordinary method if no special instructions.Said material all can make through the method for document introduction if no special instructions or obtain through commercial sources.GC representes gc among the following embodiment, and HPLC representes performance liquid chromatography, and MS representes mass spectrum, and mp representes fusing point, and cp representes clearing point, and Δ ε representes dielectric anisotropy, and Δ n representes optical anisotropy, and γ is expressed as rotary viscosity.
Embodiment 1,4-(difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-3,5-two fluoro-4 '-preparation of propyl group biphenyl
In the 250mL there-necked flask, add compound 5-bromo-2-shown in 38.9g (0.1mol) the formula II (difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-1,3-two fluorobenzene; The propylbenzene of compound shown in formula III boric acid 18g (0.11mol), 32.1g (0.275mol) soda ash light, 50ml toluene, 25ml ethanol; 25ml water, 1.15g (0.001mol) four triphenyl phosphorus close palladium, and 90 ℃ were reacted 6 hours, added 100ml toluene; 100ml water is told lower floor's water with 100ml * 2 extracted in toluene, merges organic phase; With 200ml * 3 saturated common salts washing, evaporate to dryness toluene, product decolours with silica gel column chromatography; With 3 times of ethanol and 0.5 times of sherwood oil recrystallization 2 times, obtain target compound, yield 65%.
Experimental result is following:
(1)GC：99.9％；
(2) GC-MS data analysis: 428 (M+1.5) 297 (100) 216 (50) 131 (16);
(3)mp：48℃，Δε：25.2，Δn：0.1579，γ：96。
By on can know that this compound structure is correct, be compound shown in the formula I.
Embodiment 2,2-(4 '-(difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-3 ', 5 '-DfBP)-preparation of 5-propyl group tetrahydropyrans
In the 1L there-necked flask, add compound 5-iodo-2-shown in 43.6g (0.1mol) the formula II (difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-1,3-two fluorobenzene; The 4-of compound shown in the formula III (the phenylo boric acid 27.3g (0.11mol) of 5-propyl group tetrahydropyrans-2-), 32.1g (0.275mol) soda ash light, 500ml toluene, 25ml ethanol; 25ml water, 1.25g (0.001mol) four triphenyl phosphorus close palladium, and 90 ℃ were reacted 6 hours, added 100ml toluene; 100ml water is told lower floor's water with 100ml * 2 extracted in toluene, merges organic phase; With 200ml * 3 saturated aqueous common salts washing, evaporate to dryness toluene, product decolours with silica gel column chromatography; With 3 times of ethanol and 0.5 times of sherwood oil recrystallization 2 times, obtain target compound, yield 70%.
Experimental result is following:
(1)GC：99.9％；
(2) GC-MS data analysis: 512 (M+0.5) 381 (100) 300 (30) 131 (12);
(3)mp：75℃，cp：118℃，Δε：26，Δn：0.1401，γ：300。
By on can know that this compound structure is correct, be compound shown in the formula I.
Embodiment 3,2-(4 '-(difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-2,3 ', 5 ', 6-tetrafluoro biphenyl)-preparation of 5-propyl group tetrahydropyrans
Present embodiment reference example 1 replaces with 2 with the reaction raw materials propylbenzene boric acid among the embodiment 1, and 6-two fluoro-4-(5-propyl group tetrahydropyrans 2-) phenylo boric acid prepares following compound, and yield is 72%;
(1)GC：99.9％；
(2) GC-MS data analysis: 548 (M+0.4) 417 (100) 336 (27.8) 131 (14.4);
(3)mp：83℃，Δε：35.6，Δn：0.1316，γ：457。
By on can know that this compound structure is correct, be compound shown in the formula I.
Embodiment 4,2-(6-(4 '-(difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-3 ', 5 '-DfBP) tetrahydropyrans-2-)-and 5-propyl group-1, the preparation of 3-dioxane
Present embodiment reference example 1, the reaction raw materials propylbenzene boric acid among the embodiment 1 is replaced with 4-, and (phenylo boric acid of 5-(5-propyl group-1,3-dioxane) tetrahydropyrans-2-) prepares following compound, and yield is 68%;
(1)HPLC：99.9％；
(2) LC-MS data analysis: 621 (M+23);
(3)mp：127℃，cp：251.1℃，Δε：35.6，Δn：0.1353。
By on can know that this compound structure is correct, be compound shown in the formula I.
Embodiment 5,2-(4 '-(difluoro (3,4,5-trifluoromethoxy phenoxy base) methyl)-3 ', 5 '-DfBP)-preparation of 5-propyl group octahydro pentalene
Present embodiment reference example 2 replaces with 4-(5-propyl group octahydro pentalene) phenylo boric acid with the reaction raw materials 4-among the embodiment 2 (5-propyl group tetrahydropyrans) phenylo boric acid, prepares following compound, and yield is 70%;
(1)GC：99.9％；
(2) GC-MS data analysis: 536 (M+0.6) 389 (100) 265 (10) 252 (3) 239 (3);
(3)mp：66.5℃，Δε：14.3，Δn：0.109。
Embodiment 6-26
According to embodiment 1 identical method, only replace corresponding substituting group according to the structural formula of product, obtain as shown in the formula compound shown in the I, yield all is not less than 70%:
Claims (6)
1. a method for preparing compound shown in the formula I comprises the steps: under the condition that catalyzer exists, compound shown in compound shown in the formula II and the formula III and alkali mixing to be reacted, and reaction finishes and obtains compound shown in the said formula I;
Formula II
Formula III
Formula I
In the said formula II-formula III, R all is selected from least a in the alkenyl of alkoxyl group and C2-C8 of straight chained alkyl, C1-C8 of C1-C8, and X is Br or I;
A
1, A
2And A
3All be selected from singly-bound, phenyl, fluorine substituted benzene cyclic group, pyrimidyl, pyridyl, dioxane base, at least a in THP trtrahydropyranyl and the octahydro pentalene base;
Y
1And Y
2All be selected among H and the F any one.
2. method according to claim 1 is characterized in that: said catalyzer is that four triphenyl phosphorus close palladium;
Said alkali is selected from least a in yellow soda ash, sodium hydrogencarbonate, salt of wormwood, potassiumphosphate and the sodium hydroxide, preferred yellow soda ash.
3. method according to claim 1 and 2 is characterized in that: compound shown in the said formula II is 1: 0.001～0.1 with the mole dosage ratio that feeds intake of said catalyzer, preferred 1: 0.01;
Said alkali is 1～5: 1 with the mole dosage ratio that feeds intake of compound shown in the said formula III, preferred 2.5: 1;
Compound shown in the said formula II is 1 with the mole dosage ratio that feeds intake of compound shown in the formula III: 0.8-1.5, preferred 1: 1.1.
4. according to the arbitrary described method of claim 1-3, it is characterized in that: said being reflected in the solvent carried out.
5. method according to claim 4; It is characterized in that: said solvent is selected from THF, ethanol, water, N; N N, N; At least a in N N,N-DIMETHYLACETAMIDE, toluene and the benzene is to mix the mixture that gets at 2: 1: 1 by toluene, second alcohol and water with volume ratio preferably;
The concentration of compound shown in the said formula II in said solvent is 0.5～4mol/L, preferred 1mol/L.
6. according to the arbitrary described method of claim 1-5, it is characterized in that: in the said reactions step, temperature is 70-150 ℃, and preferred 90 ℃, the time is 4-10 hour, preferred 6 hours.
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Application publication date: 20120919 |