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2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84.4%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 12h;Heating / reflux;
(7-a) Synthesis of compound 2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl represented by formula: First, 50 ml of ethanol containing 7.52 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,5-difluoro-1-nitrobenzene dissolved therein, 21.0 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.61 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 12 hours.. After the reaction, water and ether were added to the reaction solution for extraction.. The resultant ether layer was washed with a saturated brine and dried with sodium:sulfate.. The solvent was then distilled off.. The residue was purified by silica gel column chromatography (eluent:toluene/hexane=1/4) and recrystallized from hexane, to obtain 6.87 g (Y: 84.4%) of 2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl.. The purity of the resultant compound was 100.0% as measured by GC. The phase transfer temperature of the compound was as follows.
4-bromo-2-methylphenyl methoxymethyl ether[ No CAS ]
4'-(trans-4-pentylcyclohexyl)-3-methylbiphenyl-4-yl methoxymethyl ether[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80.2%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 5h;Heating / reflux;
First, 125 ml of ethanol containing 21.1 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved-therein, 125 ml of benzene containing 16.2 g of 4-bromo-2-methylphenyl methoxymethyl ether obtained from the synthesis (9-c) above dissolved therein, 77.0 ml of a sodium carbonate aqueous solution at a concentration of 2 mol/l, and 2.02 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 500 ml flask, and stirred under reflux for five hours. After the reaction, water and toluene were added to the reaction solution for extraction. The resultant toluene layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography(eluent:toluene/hexane=1/1),to obtain 21.36 g (Y: 80.2%) of 4'-(trans-4-pentylcyclohexyl)-3-methylbiphenyl-4-yl methoxymethyl ether. The purity of the resultant compound was 97.2% as measured by GC.
4-bromo-2-fluoro-4'-(trans-4-pentylcyclohexyl)biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67.8%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 37h;Heating / reflux;
First, 150 ml of ethanol containing 17.84 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 150 ml of benzene containing 15.0 g of 4-bromo-2-fluoro-1-iodobenzene dissolved therein, 49.8 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 1.44 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 500 ml flask, and stirred under reflux for 37 hours. After the reaction, water and ether were added to the reaction solution for extraction. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:hexane) and recrystallized from hexane, to obtain 13.6 g (Y: 67.8%) of 4-bromo-2-fluoro-4'-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 99.5% as measured by GC.
4-bromo-2,6-difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
39.1%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 48h;Heating / reflux;
(5-a) Synthesis of compound 4-bromo-2,6-difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl represented by formula: First, 50 ml of ethanol containing 5.61 g of 4-(trans-4-pentylcyclohexyl)phenylboronic acid dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,6-difluoro-1-iodobenzene dissolved therein, 15.7 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.45 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 48 hours.. After the reaction, water and ether were added to the reaction solution for extraction.. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate.. The solvent was then distilled off.. The residue was purified by silica gel column chromatography (eluent:hexane) and recrystallized from acetone, to obtain 2.58 g (Y: 39.1%) of 4-bromo-2,6-difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl.. The purity of the resultant compound was 100.0% as measured by GC. (5-b) Synthesis of polymerizable compound 2,6-difluoro-4'-(trans-4-pentylcyclohexyl)-4-vinylbiphenyl represented by formula (E) above First, 2.58 g of 4-bromo-2,6-difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl obtained from the synthesis (5-a) above, 2.33 g of tributylvinyltin, 0.18 g of tetrakis(triphenylphosphine)palladium(0), 0.008 g of p-methoxyphenol, and 50 ml of anhydrous toluene were put in an argon-replaced 300 ml flask, and stirred under reflux for nine hours..
4-amino-4'-(trans-4-pentylcyclohexyl)-3-trifluoromethylbiphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91.3%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 6h;Heating / reflux;
First, 100 ml of ethanol containing 4.91 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 100 ml of benzene containing 10.0 g of 2-trifluoromethyl-4-bromoaniline, 41.7 ml of a sodium carbonate aqueous solution with a concentration of 2 mol/l, and 1.20 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 300 ml flask, and stirred under reflux for six hours. After the reaction, water and ether were added to the reaction solution for extraction. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:hexane/toluene=4/1), to obtain 14.82 g (Y: 91.3%) of 4-amino-4'-(trans-4-pentylcyclohexyl)-3-trifluoromethylbiphenyl. The purity of the resultant compound was 99.2% as measured by GC.
4'-(trans-4-pentylcyclohexyl)-2-trifluoromethyl-4-nitrobiphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91.3%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 12h;Heating / reflux;
First, 100 ml of ethanol containing 6.57 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 100 ml of benzene containing 10.0 g of 2-trifluoromethyl-4-nitrobromobenzene dissolved therein, 37 ml of a sodium carbonate aqueous solution with a concentration of 2 mol/l, and 1.07 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 300 ml flask, and stirred under reflux for 12 hours. After the reaction, water and ether were added to the reaction solution for extraction. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography (eluent:hexane/toluene=4/1), to obtain 14.2 g (Y: 91.3%) of 4'-(trans-4-pentylcyclohexyl)-2-trifluoromethyl-4-nitrobiphenyl. The purity of the resultant compound was 100.0% as measured by GC.
2-fluoro-6-[4-(trans-4-pentylcyclohexyl)-phenyl]pyrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
3a In an analogous reaction to Example 1b, 2.17 g (16.41 mmol) of 2-chloro-6-fluoropyrazine (prepared as described in Example 1a) and 4.50 g (16.41 mmol) of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> gives 3.36 g of 2-fluoro-6-[4-(trans-4-pentylcyclohexyl)-phenyl]pyrazine. STR19 3b
4.4 g of 4-bromophenol in a 500 mL three-necked flask(25.5 mmol),7.0 g (25.5 mmol) of 4- (trans-4-pentylcyclohexyl) phenylboronic acid,300 mL of dimethoxyethane,Charge 40 mL of 2 M aqueous solution of potassium carbonate, under nitrogen atmosphere,Stir for 10 minutes.Tetrakis (triphenylphosphine) palladium (0)2. 9 g (2.6 mmol) was added and stirred for 12 hours while heating at 85 C.30 mL of 1 M hydrochloric acid was added, and extracted with chloroform.The organic layer is saturated with 200 mL of multi-layered water,After washing twice with 100 mL of water,Dried over magnesium sulfate and filtered.After concentrating the filtrate with an evaporator,The resulting residue was purified by column chromatography to obtain 1.9 g of Intermediate 9-1 (yield 24%).