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4-chloro-3-fluoro-4'-(p-n-propylphenyl)-biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In toluene;
EXAMPLE 1 A mixture of 0.1 mole of 4'-n-propyl-4-biphenylboronic acid (obtained by the reaction of the Grignard reagent of 4'-n-propyl-4-bromobiphenyl and trimethyl borate), 0.1 mole of 4-chloro-3-fluorobromobenzene, tetrakis (triphenylphosphine) palladium (1 mole %), 2 m sodium carbonate solution (150 ml), toluene (250 ml) and IMS (60 ml) is stirred and refluxed for 16 hrs under a nitrogen atomosphere. After usual work-up 4-chloro-3-fluoro-4'-(p-n-propylphenyl) -biphenyl is obtained.
[Experimental embodiment 2]: preparation of the compound in formula (I-4)Step 1: synthesize the compound in formula (2-A) (hereinafter ?compound (2-A)?).First, 10 grams of 4-bromo-1-propyl benzene in formula (2) is placed in a two-neck bottle. The two-neck bottle is heated, and waterless THF is injected into the two-neck bottle. After the two-neck bottle is cooled to -78 C., 18 mL of an n-BuLi solution is slowly dripped into the two-neck bottle. After maintaining the reaction temperature at -78 C. for 1 hour, 10 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is slowly dripped into the two-neck bottle. After continuing the reaction for 1 hour, the bottle is heated to room temperature. 10 mL of distilled water is added to the above double-neck bottle, and low pressure evaporation-concentration is performed to remove the THF. Ethyl acetate and distilled water are used to extract the obtained mixture solution. Afterwards, the collected organic solution is desiccated by waterless magnesium sulfate, and the solid magnesium sulfate is removed by gravitational filtration. Then, low pressure evaporation-concentration is performed on the obtained mixture solution to remove the solvent. 9.47 grams of a white solid compound (2-A) is obtained. The yield is 80%.
With potassium carbonate In water; toluene for 18h; Heating;
2.2
Step 2: synthesize the compound in formula (2-B) (hereinafter “compound (2-B)”).Next, 9.47 grams of the compound (2-A), 5.58 grams of 4-bromo-2-fluorobenzenamine, 12.2 grams of potassium carbonate, 30 mL of distilled water, 150 mL of toluene, and 0.5 mL Aliquate 336 which is used as a surfactant are placed in a 250 mL double-neck bottle. After heating the double-neck bottle until convection occurs, 0.5 mL of tetrakis(triphenylphosphine)palladium (0) which is used as a catalyst is added to the double-neck bottle. The bottle is heated for another 18 hours with convection. After the reaction is complete, the bottle is cooled to room temperature, and the mixture solution is extracted by ethyl acetate and distilled water. After all the collected organic solution is desiccated by waterless magnesium sulfate, gravitational filtration is performed to remove the solid magnesium sulfate, and low pressure evaporation-concentration is performed to remove the solvent. The obtained product is dissolved in 15 mL of dichloromethane, and 150 mL of hexane is used for further precipitation. Aspiration filtration is then performed to collect solid materials, thereby obtaining 7 grams of a yellow solid compound (2-B). The yield is 78%.
Stage #1: [4'-propyl-1,1'-biphenyl-4-yl]boronic acid; 4-bromo-phenol With potassium carbonate In water; acetone for 0.333333h; Inert atmosphere; Reflux;
Stage #2: With palladium diacetate In water; acetone for 6h; Inert atmosphere; Reflux;
Stage #1: [4'-propyl-1,1'-biphenyl-4-yl]boronic acid; 3-fluoro-4-methoxyphenyl bromide With potassium carbonate In water; acetone for 0.333333h; Inert atmosphere; Reflux;
Stage #2: With palladium diacetate In water; acetone for 6h; Inert atmosphere; Reflux;
Stage #1: 1-ethoxy-2,3-difluoro-4-iodobenzene; [4'-propyl-1,1'-biphenyl-4-yl]boronic acid With potassium carbonate In water; acetone for 0.333333h; Inert atmosphere; Reflux;
Stage #2: With palladium diacetate In water; acetone for 6h; Inert atmosphere; Reflux;
1-1
(1-1) Under a dry nitrogen atmosphere, metal magnesium (2.6 g) was suspended in THF(10 mL), and solution of 4- (4-propylphenyl) bromobenzene (25 g) dissolved inTHF (100 mL) was slowly added at a rate at which the system is gentle to reflux and then stirredfor 1 hour at room temperature. Then, after slowly added triisopropyl borate(10.4g) under ice-cooling, the mixture was stirred for 30 minutes at room temperature. Again cooled with ice, and 10% hydrochloric acid (100 mL) was added slowly and separated, and the aqueous layer was extracted by adding THF(100 mL), and the combined organic layers were washed twice with saturated brine (100 mL), and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, to give the crude 4- (4-propylphenyl)phenylboronic acid (26.6g).
2,3,5-trifluoro-1-[4-(4-propylphenyl)phenyl]benzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
18.0 g
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; for 15h;Inert atmosphere; Reflux;
(1-2)Under a dry nitrogen atmosphere, the crude 4-(4-propylphenyl) phenylboronic acid (26.6 g) obtained in (1-1),2,3,5-trifluoro-bromobenzene (19.2 g ) potassium carbonate (18.8 g), tetrakis(triphenylphosphine) palladium (0) (2.10 g) and ethanol (200 mL) were mixed,and stirred for 15 hours at a temperature at which solvent is refluxed. Aftercooling to room temperature, the precipitated crystals were filtered and driedunder reduced pressure, and dissolved in mixed solvent (toluene / hexane = 2:1,150mL) and the solution was purified by silica gel column chromatography. Thesolvent was evaporated under reduced pressure, and recrystallized from a mixedsolvent of toluene and hexane, to obtain 2,3,5-trifluoro-1- [4-(4-propylphenyl) phenyl] benzene (18.0 g).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water for 8h; Reflux;
3.1 STEP 1
100mlIn a three-necked flask, 30 ml of toluene, 13 ml of ethanol, 12 g of 4'-propylbiphenylboronic acid (compound I-3)(Compound II-3), 30 ml of water, 11 g of sodium carbonate and 0.3 g of tetrakis (triphenylphosphine) palladium were added and the mixture was heated to reflux,The reaction was stopped for 8 hours under reflux. Cooling to 45 ° C, standing still liquid, the lower aqueous phase extracted with toluene twice, each 100ml,Organic phase, the combined organic phase washed twice with water, each 200ml, washed to PH = 7-8, the pump vacuum distillation solvent, leftThe residue was passed through a column of silica gel, eluted with a mixture of ethyl acetate and petroleum ether. The eluent was collected and the solvent was evaporated under reduced pressure.Ethyl ether and petroleum ether to give 13 g of compound III-3 as a gray powder in 99.9% yield of 90.4%.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 48h; Inert atmosphere; Reflux;
(0143) Manufacturing Method of Liquid Crystal Compound 3PPI of
(0143) Manufacturing Method of Liquid Crystal Compound 3PPI of (0144) Firstly, 3.55 g (0.015 mol) of Compound 1, 10.8 g (0.045 mol) of Compound 15 (4′-propyl-biphenyl-4-yl) boronic acid, 16.584 g (0.12 mol) of K2CO3, 50 mL of THF, and 5 mL of water were added into a reaction bottle. Then, 0.2 g of tetra(triphenylphosphine)palladium (Pd[P(Ph)3]4) was slowly added into the reaction bottle under nitrogen. Then, the mixture in the reaction bottle was heated to reflux under nitrogen for 48 hours. After the reaction completed, an extraction was performed by using ethyl acetate (EA)/sodium chloride aqueous solution. The organic phase of the extraction solution was collected and concentrated. A column chromatography was performed by using hexane as a mobile phase. The mobile phase after column chromatography was concentrated by the rotary concentrator, and the crude product was obtained. Then, the crude product was recrystallized by using 20 mL of toluene and 50 mL anhydrous alcohol as the solvent, and liquid crystal compound 3PPIof(white solid) was obtained. The final product may be changed by using different Compound 15 (such as, 2PPIof may be obtained by choosing (4′-ethyl-biphenyl-4-yl) boronic acid as Compound 15). The reaction is as follows
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; N,N-dimethyl-formamide; for 4h;Sealed tube; Inert atmosphere; Reflux;
Set the reflux reaction device, put the stirrer into the reaction flask, add 4-propylbiphenylboronic acid, 2, 6-difluoro-4-bromoaniline, catalyst Pd (Pph3) 4, cesium carbonate; Sealing the reaction system, replacing the air in the sealing system into nitrogen; N, N-dimethylformamide and water were added, stirred and slowly heated to reflux, to ensure that the system was reacted under nitrogen. After 4 hours, the degree of reaction was measured with TLC.
With sodium carbonate In ethanol; water; toluene at 73℃; for 10h; Inert atmosphere;
2.1 (1) Synthesis of compound BYLC-02-1
Under the protection of nitrogen, add 40.0g compound BYLC-01-1, 34.6g 4'-propyl-4-biphenylboronic acid, 15.3g sodium carbonate, 200ml toluene, 80ml ethanol into the reaction flask,80ml water, start stirring, add 0.3g Pd0132, heat to 73°C and react for 10h, After conventional post-treatment, ethanol was recrystallized to obtain a white solid (compound BYLC-02-01), 48.4 g, LC: 97.8%, yield: 85.6%.
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