Name: 23674-20-6|9-Bromo-10-phenylanthracene|98%
Brand: Ambeed
SKU: A111145
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1
[ 602-55-1 ]
[ 23674-20-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-Bromosuccinimide; In chloroform; at 60℃; for 1h;Inert atmosphere;	9-phenylanthracene (1) (2.54 g, 10.0 mmol), N-bromosuccinimide (2.14 g, 12.0 mmol) and chloroform (200 mL) were heated at 60 C. for 1 hour under a nitrogen atmosphere. After cooling to room temperature, the solvent was distilled off under reduced pressure. After re-dissolving in acetone, it was reprecipitated in methanol and filtered to obtain a yellow solid (3.26 g, yield 98%).
94%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 19h;Inert atmosphere;	Under an argon stream, 24.58 g (96.7 mmol) of the compound (1-8) synthesized by the above reaction was dissolved in 500 ml of dehydrated dimethylformamide, and cooled in an ice bath. 100 ml of dehydrated dimethylformamide solution containing 106.4 mmol of N-bromosuccinimide was added dropwise over 1 hour and the mixture was stirred at room temperature for 18 hours. Water and methanol were added to the reaction solution, the precipitated solid was filtered and washed with methanol. The obtained solid was dried under reduced pressure, and a white powder (yield 30.26 g, yield 94%) of the target compound (1-9) was obtained.
91%	With N-Bromosuccinimide; In chloroform; at 80℃; for 12h;	Compound A (8.0 g, 31.5 mmol) was dissolved in chloroform (150 mL), NBS (5.8 g, 32.6 mmol) was added, and the mixture was refluxed at 80 C for 12 hours. After completion of the reaction, the solid formed during the reaction was filtered, washed with distilled water and dried to synthesize Compound F (9.5 g, 91%).

90%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 12h;Inert atmosphere; Reflux;	To a round bottom flask, intermediate (C) 25.0g (98.30mmol), into the NBS 19.24g (108.13mmol) was dissolved was added to stirred DMF (393ml). Reflux and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction after the solid filter precipitate was poured in 5L DIW, dried and filtered to extract and then extracted with methylene chloride to dissolve the magnesium sulfate, filtered,The solution was concentrated under reduced pressure. The product n- hexane / dichloromethane (7: 3 by volume) was purified by a silica gel column chromatography to give the intermediate (D) as 29.48g (90% yield).
90%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 12h;Reflux; Inert atmosphere;	To a round bottom flask, intermediate (C) 25.0g (98.30mmol), for putting the NBS 19.24g (108.13mmol) was added to DMF (393ml)After it was stirred. Reflux and stirred for 12 hours under a nitrogen atmosphere. After the reaction was poured into precipitation 5L DIWFilter the solid after which the extract was filtered, dried and then extracted with methylene chloride, dissolved magnesium sulfate, and WThe gwaaek was concentrated under reduced pressure. With: (3 volume ratio 7) by column chromatography on silica gel, the product n- hexane / dichloromethaneTo give the aimed compound intermediate (D) to give a 29.48g (90% yield).
89%		Next, a synthetic method of 9-bromo- 10-phenylanthracene from 9-phenylanthracene will be described. 6.0 g (23.7 mmol) of 9-phenylanthracene prepared by the above method is dissolved in 80 mL of carbon tetrachloride, carbon tetrachloride solution (10 mL) containing 3.80 g (21.1 mmol) of boron is dropped from a dropping funnel into the reaction solution. After the dropping, it is agitated at room temperature. A sodium thiosulfate solution is added to stop the reaction. The organic layer is rinsed with sodium hydroxide solution and saturated salt solution, and dried with magnesium sulfate. After natural filtration, it is condensed and dissolved in toluene, and filtered through Florisil, celite. When the filtrate is condensed, and recrystallized with dichloromethane and hexane, 7.0 g of 9-bromo- 10-phenylanthracene is obtained as a light yellow solid at a yield of 89 %. A synthetic scheme of 9-bromo- 10-phenylanthracene from 9-phenylanthracene is shown below
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	First, 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride. Then, a solution in which 3.80 g (21.1 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped in the reactive solution by using a dropping funnel. After the dropping, the mixture was stirred at a room temperature for one hour. After the reaction, the reaction was stopped by adding a sodium thiosulfate aqueous solution. An organic layer was washed with a sodium hydroxide aqueous solution and saturated saline in this order. After the washing, the product was dried with magnesium sulfate. After the product was naturally filtrated, the filtrate was concentrated and then was dissolved in toluene. Thereafter, this solution was filtrated through florisil, celite, and alumina. After the filtrate was concentrated, the concentrated filtrate was recrystallized by dichloromethane and hexane. Thus, 7.0 g (yield: 89%) of a light yellow solid of 9-bromo-10-phenylanthracene, which was target matter, was obtained (synthetic scheme (b-4)).
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	(ii) Synthesis of 9-bromo-lO-phenylanthracene.; 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, and then in the reaction solution thereof, a solution in which 3.80 g (21.1 EPO <DP n="54"/>mmol) of bromine dissolved in 10 mL of carbon tetrachloride was dropped by a dropping funnel. After dropping, it was stirred for one hour at room temperature. After reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a NaOH aqueous solution and saturated saline, and then dried with magnesium sulfate. After natural filtration, a filtrate was condensed and dissolved in toluene, and then filtration was carried out using Florisil, celite, and alumina. When the filtrate was condensed and then recrystallized with dichloromethane and hexane, 7.0 g of 9-bromo-lO-phenylanthracene that is a target substance was obtained as a light yellow solid at a yield of 89%
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	(ii) Synthesis of 10-bromo-9-phenylanthracene Synthetic Scheme (f-2) of 10-bromo-9-phenylanthracene is shown below. 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved into 80 mL of carbon tetrachloride, and a solution in which 3.80 g (21.1 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped into the reaction solution using a dropping funnel. After dropping, the solution was stirred for 1 hour at a room temperature. After the reaction, an aqueous sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with an aqueous sodium hydroxide (NaOH) solution and a saturated sodium chloride solution and dried with magnesium sulfate. The mixture was naturally filtered, and a compound obtained by concentrating the filtrate was dissolved into toluene and filtered through florisil, Celite, and alumina. The filtrate was concentrated and recrystallized with dichloromethane and hexane, thereby obtaining 7.0 g of objective 10-bromo-9-phenylanthracene as a light-yellow solid with a yield of 89%.
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	(ii) Synthesis of 10-bromo-9-phenylanthracene The following shows a synthesis scheme (f-2) of 10-bromo-9-phenylanthracene. After 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, a solution of 3.80 g (21.1 mmol) of bromine dissolved in 10 mL of carbon tetrachloride was dripped through a dropping funnel into the reaction solution. After the dripping, the solution was stirred at room temperature for one hour. After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium hydroxide (NaOH) aqueous solution and a saturated saline solution and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated, dissolved in toluene, and filtered through Florisil, Celite, and alumina. When the filtrate was concentrated and recrystallized with dichloromethane and hexane, 7.0 g of a light yellow solid of 10-bromo-9-phenylanthracene that was an object was obtained (yield: 89%).
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 ml of carbon tetrachloride. A solution of 3 80 g (21.1 mmol) of bromine dissolved in 10 ml of carbon tetrachloride was delivered dropwise into that reaction solution by a dropping funnel. After the dropping was complete, the mixture was stirred for 1 hour at room temperature. After the reaction, a sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with a NaOH solution and a saturated saline solution, and dried with magnesium sulfate. After natural filtration, concentration and dissolving in toluene were conducted. Then, filtration was done through Florisil, Celite and alumina. The filtrate was concentrated," then recrystallized with dichloromethane and hexane. The target substance, 9-bromo-10-phenylanthracene, was obtained in the form of a pale yellow solid, weighing 7.0 g in a yield of 89% (synthesis scheme 0-4)). [0410]
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	2) Synthesis of 9-bromo-lO-phenylanthracene6.0 g (24 mmol) of 9-phenylanthracene obtained by the above Step 1(1) was dissolved in 80 mL of carbon tetrachloride. Then, the mixture was stirred while dropping a solution in which 3.8 g (21 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride, using a dropping funnel. After the dropping, this mixture was further stirred at room temperature for 1 hour to be reacted. After the reaction, sodium thiosulfate solution was added into the reaction solution, and the mixture was stirred. After that, an organic layer thereof was washed with aqueous sodium hydroxide and saturated saline in this order. Then, magnesium sulfate was added to the organic layer, so that the moisture was removed. This suspending solution was naturally filtered, so that a filtrate was obtained. The obtained filtrate was concentrated, dissolved in toluene, and filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was concentrated and recrystallized with a mixed solvent of dichloromethane and hexane, whereby 7.0 g of a light-yellow solid of 9-bromo-10-phenylanthracene, which was the object of the <n="127"/>synthesis, was obtained in a yield of 89 % (synthesis scheme (a-2)).
89%	With bromine; In tetrachloromethane; toluene;	(ii) Synthesis of 10-bromo-9-phenylanthracene The following shows Synthesis Scheme (F-2) of 10-bromo-9-phenylanthracene. After 6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, a solution of 3.80 g (21.1 mmol) of bromine dissolved in 10 mL of carbon tetrachloride was dropped through a dropping funnel into the reaction solution. After the dropping, the solution was stirred at room temperature for one hour After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium hydroxide (NaOH) aqueous solution and saturated saline and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated, dissolved in toluene, and filtered through Florisil, Celite, and alumina. When the filtrate was concentrated and recrystallized with dichloromethane and hexane, 7.0 g of a light-yellow solid of 10-bromo-9-phenylanthracene, which is a target matter, was obtained with a yield of 89%.
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	(2) Synthesis of 9-bromo-lO-phenylanthracene; 6.0 g (23.7 mmol) of 9-phenylanthracene synthesized by the above method was dissolved in 80 mL of carbon tetrachloride. A solution of 3.80 g (21.1 mmol) of bromine in 10 mL of carbon tetrachloride was dripped into the reaction solution using a dropping funnel. After the completion of dripping, the mixture was stirred for one hour at a room temperature. An aqueous sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with an aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution in this order. After washing, the organic layer was dried with magnesium sulfate and then filtered naturally. After concentrating, the organic layer was dissolved in toluene. Then, the solution was filtered through florisil, Celite, and alumina. After concentrating the filtrate, the filtrate was recrystallized with dichloromethane and hexane, thereby obtaining 7.0 g of 9-bromo-10-phenylanthracene as a light yellow solid (yield: 89 %). A synthesis scheme of 9-bromo-10-phenylanthracene from 9-phenylanthracene is shown below.
89%	With bromine; In tetrachloromethane; at 20℃; for 1h;	6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, and then in the reaction solution thereof, a solution in which 3.80 g (21.1 mmol) of bromine dissolved in 10 mL of carbon tetrachloride was dropped with a dropping funnel. After dropping, it was stirred for 1 hour at room temperature. After reaction, a sodium thiosulfate solution was added and stirred. Then an organic layer was washed with aqueous sodium hydroxide and saturated saline, and then dried with magnesium sulfate. After a mixed solution was naturally filtered, a filtrate was concentrated and dissolved in toluene, and then filtration was carried out through florisil, celite, and alumina. When a filtrate was concentrated and then recrystallized with a mixture of dichloromethane and hexane, 7.0 g of 9-bromo-10-phenylanthracene that was a target substance and was a light yellow solid was obtained in a yield of 89 % (Synthesis Scheme (b-2)).
89.3%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 6h;	Exemplary Synthesis 2; Synthesis of Compound 2; Synthesis of 10-Phenylanthracene-9-Boronic Acid; An amount of 15.14 g (58.9 mmol) of 9-bromoanthracene, 7.2 g (59 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 100 ml of toluene and 25 ml of ethanol. Then, 50 ml of 2M sodium carbonate solution was added to the mixed solvent and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 13.65 g (53.7 mmol) of 9-phenylanthracene. The yield was 91.2%.An amount of 13.65 (53.7 mmol) of 9-phenylanthracene was dissolved in 100 ml of N,N dimethylformamide. An amount of 10.5 g (59 mmol) of N bromosuccinimide was added and allowed to react for six hours. Then, distilled water was added to stop the reaction and the deposit was filtered. The recovered deposit was purified by column chromatography to obtain 15.97 g (48 mmol) of 9-bromo-10-phenylanthracene. The yield was 89.3%.An amount of 14 g (42 mmol) of 9-bromo-10-phenylanthracene was dissolved in dehydrated THF and cooled to -80 C. Then, 31.2 ml (49 mmol) of a solution of n-butyllithium in n-hexane was added dropwise. Forty minutes later, 13 g (89 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was added and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 10 g (33.6 mmol) of 10-phenylanthracene-9-boronic acid. The yield was 75.2%.(Synthesis of Compound 2); An amount of 0.94 g (3.14 mmol) of 10-phenylanthracene-9-boronic acid, 1.52 g (3.14 mmol) of 9-bromo-7,12-diphenybenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.37 g (2.09 mmol) of Compound 2. The yield was 66.6%.The obtained Compound 2 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
89%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 85℃; for 11h;Inert atmosphere;	(2) 9 - Benzene anthracene brominated: will be 9 - benzene anthracene 2.15 g, DMF 100 ml, NBS 1.80 g is added to the reaction bottle, then the system vacuum, under the protection of nitrogen 85 C reaction 1 hours. After the completion of the reaction, methanol washing, filtered to obtain product 9 - bromo -10 benzene anthracene. Yield 89%.
89.8%	With bromine; In dichloromethane; at 0℃; for 1h;Inert atmosphere;	<1-b> was synthesized by the following Scheme 2. In a 5000 mL round bottom flask, 170.0 g (0.668 mol) of <1-a> obtained from Scheme 1 was dissolved in 1360 mL of methylene chloride, and the temperature of the reaction was lowered to 0 under nitrogen and stirred for 30 minutes.117.50 g (0.735 mol) of bromine (Br2) diluted in 600 mL of methylene chloride was slowly added dropwise for 1 hour. After dropping, the temperature inside the reactor was raised to room temperature. After completion of the reaction, the reaction solution was basified with an aqueous solution of sodium thiosulfate (Na2S2CO3), the aqueous layer was removed by layer separation, and the organic layer was concentrated under reduced pressure.After concentration under reduced pressure, methanol was added to precipitate and solid. 200.0g (yield 89.8%) <1-b> was obtained.
88%	With N-Bromosuccinimide; In chloroform; for 3h;Reflux;	The compound (1) 4.1 g (16.1 mmol) and NBS 3.16 g(17.7 mmol) were put into the chloroform 150 mL and itmixed reflux for 3hours. The reaction solution was washed with the water 200 mL after doing the cooling in a room temperature and it filtered to the Magnesium Sulfate Anhydrous. The residue was melted with the dichloromethane after concentration under reduced pressure is performed to the filter liquor and it recrystallized to the methanol and it dried and the compound (2) 4.71 g(yield 88%) was obtained with filtering.
87%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 88℃; for 1.5h;Inert atmosphere;	Bromination of 9-phenylanthracene: 9-phenylanthracene 2.15 g, DMF 100 mL, and NBS 1.80 g were placed in a reaction flask, and then the system was evacuated, and reacted at 88 C for 1.5 hour under a nitrogen atmosphere.After the reaction is over, the methanol is washed.The product 9-bromo-10-phenylanthracene was obtained by suction filtration.The yield was 87%.

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[ 23674-20-6 ]
[ 150712-74-6 ]

Yield	Reaction Conditions	Operation in experiment
96%		(iii) Synthesis method of 9-iodine-10-phenylanthracene 10 g (30 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was put into a 500 mL three-necked flask. Then, the atmosphere in the flask was substituted with nitrogen. 200 mL of tetrahydrofuran (abbreviation: THF) was added thereto. Thereafter, the flask was put into a constant low temperature bath and the reaction solution was cooled to -40 C. After 36 mL (23 mmol) of n-butyllithium (1.54 mol/L hexane solution) was dropped into this solution, the solution was stirred at -40 C. for 1 hour to be reacted. After the solution was stirred, a solution obtained by dissolving 9.1 g (39 mmol) of iodine in 40 mL of THF was dropped into the reaction solution for 1 hour with the temperature kept at -40 C. Then, the reaction solution was stirred for 1 hour with the temperature kept at -40 C. Thereafter, the flask Was taken out from the constant low temperature bath and the reaction solution was stirred for 24 hours to be returned to room temperature. Thereafter, about 100 mL of an aqueous sodium thiosulfate solution was added to the reaction solution to complete the reaction. An organic layer of the mixture was washed with water and a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. After the drying, the mixture was subjected to suction filtration, and the filtrate was condensed to obtain a residue. The obtained residue was dissolved in toluene and subjected to suction filtration through Florisil, celite, and then alumina. The filtrate was condensed; then 29 g of objective 9-iodine-10-phenylanthracene was obtained as a yellow solid in a yield of 96%. A synthetic scheme of 9-iodine-10-phenylanthracene is illustrated below (synthetic scheme b-3).
83%		Next, a synthetic method of 9-iodo-lO-phenylanthracene using 9-bromo -10-phenylanthracene prepared by the above method as a starting material will be shown. 3.33 g (10 mmol) of 9-bromo- 10-phenylanthracene was dissolved in THF 80 mL, and cooled to -78 0C, and n-BuLi (1.6 M, 7.5 mL,12.0 mmol) is thereafter dropped and agitation is carried out for one hour. Subsequently, THF solution (20 mL) containing 5g (20.0 mmol) of iodine is dropped at -78 0C, and agitated for 2 hours. After the reaction, a sodium thiosulfate solution is added to stop the reaction. The organic layer is rinsed with sodium thiosulfate solution and saturated salt solution, and dried with magnesium sulfate. After natural filtration, when the filtrate is condensed and thereafter recrystallized with ethanol, 3.1 g of 9-iodo- 10-phenylanthracene is obtained as a light yellow solid at a yield of 83 %. A synthetic scheme of 9-iodo- 10-phenylanthracene from 9-bromo -10-phenylanthracene is shown below.
83%		First, 3.33 g (10 mmol) of 9-bromo-lO-phenylanthracene was dissolved in 80 niL of tetrahydrofuran (abbreviation: THF). Thereafter, the mixture was cooled to -78C, and then 7.5 mL (12.0 mmol) of n-butyllithium (1.6 M) was dropped in the reactive solution by using a dropping funnel. Thereafter, the mixture was stirred for one hour. A solution in which 5 g (20.0 mmol) of iodine was dissolved in 20 mL of THF was dropped. Afterwards, the mixture was stirred at -78C for 2 hours. After the reaction, the reaction was stopped by adding a sodium thiosulfate aqueous solution. Then, an organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline in this order. After the washing, the organic layer was dried with magnesium sulfate. After the product was naturally filtrated, the filtrate was concentrated. The thus-obtained solid was recrystallized by ethanol. Thus, 3.1 g (yield: 83%) of a light yellow solid of 9-iodine-10-phenylanthracene, which was target matter, was obtained (synthetic scheme (b-5)).

83%		(iii) Synthesis of 9-iodo-lO-phenylanthracene.; 3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF), and cooled to -78C. Then, in a reaction solution thereof, 7.5 mL (12.0 mmol) of n-BuLi (1.6 M) was dropped by a dropping funnel and then stirred for one hour. A solution in which 5 g (20.0 mmol) of iodine dissolved in 20 mL of THF was dropped therein, and the further stirred for 2 hours at -78C. After reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline, and then dried with magnesium sulfate. When a filtrate was condensed after natural filtration and then recrystallized with ethanol, 3.1 g of 9-iodo-10-phenylanthracene that is a target substance was obtained as a light yellow solid at a yield of 83%
83%		(iii) Synthesis of 9-iodo-10-phenylanthracene Synthetic Scheme (f-3) of 9-iodo-10-phenylanthracene is shown below. 3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved into 80 mLof tetrahydrofuran (abbr.: THF) and cooled to -78 C., and then 7.5 mL (12.0 mmol) of n-BuLi (1.6 mol/L) was dropped into the reaction solution using a dropping funnel and stirred for 1 hour. A solution in which 5 g (20.0 mmol) of iodine was dissolved in 20 mL of THF was dropped and further stirred for 2 hours at -78 C. After the reaction, an aqueous sodium thiosulfate solution was added to stop the reaction. An organic layer was washed with an aqueous sodium thiosulfate solution and a saturated sodium chloride solution and dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, and the obtained solid was recrystallized with ethanol, thereby obtaining 3.1 g of objective 9-iodo-10-phenylanthracene as a light-yellow solid with a yield of 83%.
83%		(iii) Synthesis of 9-iodo-10-phenylanthracene The following shows a synthesis scheme (f-3) of 9-iodo-10-phenylanthracene. After 3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF) and cooled to -78 C., 7.5 mL (12.0 mmol) of n-BuLi (1.6 mol/L) was dripped through a dropping funnel into the reaction solution, and the mixture was stirred for one hour. Subsequently, a solution of 5 g (20.0 mmol) of iodine dissolved in 20 mL of THF was dripped, and the solution was stirred further at -78 C. for 2 hours. After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate aqueous solution and a saturated saline solution and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated and recrystallized with ethanol; thus, 3.1 g of a light yellow solid of 9-iodo-10-phenylanthracene that was an object was obtained (yield: 83%).
83%		3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in 80 ml of tetrahydrofuran (abbrev.: THF). After bringing the temperature to -780C, 7.5 ml (12.0 mmol) of n-BuLi (1.6M) was added to the reaction solution dropwise with a dropping funnel, and the mixture was stirred for 1 hour. A solution of 5 g (20.0 mmol) of iodine EPO <DP n="117"/>dissolved in 20 ml of THF was added dropwise, and the mixture was stirred for another 2 hours at -78C. After the reaction, a sodium thiosulfate solution was added and the reaction was stopped. The organic layer was washed with a sodium thiosulfate solution and a saturated saline solution, and dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, and the solid obtained was recrystallized with ethanol. The target substance of 9-iodo-lO-phenylanthracene was obtained as a pale yellow solid, weighing 3.1 g in a yield of 83% (synthesis scheme Q-S)). [0412]
83%	With n-butyllithium; magnesium sulfate; sodium thiosulfate; In tetrahydrofuran; iodine;	(3) Synthesis of 9-iodine-10-phenylanthracene In a nitrogen atmosphere, 3.3 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> obtained by the above Step 1(2) was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF) and the temperature of the atmosphere was cooled to -78 C. Then, 7.5 mL (12 mmol) of n-butyllithium (abbreviation: n-BuLi) (1.6 mol/L hexane solution) was dropped using a dropping funnel, and this mixture was stirred for 1 hour. Then, a solution in which 5.0 g (20 mmol) of iodine was dissolved in 20 mL of THF was dropped into the mixture, and this mixture was further stirred at -78 C. for 2 hours to be reacted. After the reaction, sodium thiosulfate solution was added into the reaction solution, and the mixture was stirred. After that, an organic layer thereof was washed with sodium thiosulfate solution and saturated saline in this order. Then, magnesium sulfate was added to the organic layer, so that the moisture was removed. This suspending solution was filtered, so that a filtrate was obtained. The obtained filtrate was concentrated to provide a solid. The obtained solid was recrystallized with ethanol, whereby 3.1 g of a light-yellow solid of 9-iodine-10-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 83% (synthesis scheme (a-3)).
83%		3) Synthesis of 9-iodine-lO-phenylanthraceneIn a nitrogen atmosphere, 3.3 g (10 mmol) of 9-bromo-lO-phenylanthracene obtained by the above Step 1(2) was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF) and the temperature of the atmosphere was cooled to -78 0C. Then, 7.5 mL (12 mmol) of n-butyllithium (abbreviation: n-BuLi) (1.6 mol/L hexane solution) was dropped using a dropping funnel, and this mixture was stirred for 1 hour. Then, a solution in which 5.O g (20 mmol) of iodine was dissolved in 20 mL of THF was dropped into the mixture, and this mixture was further stirred at -78 0C for 2 hours to be reacted. After the reaction, sodium thiosulfate solution was added into the reaction solution, and the mixture was stirred. After that, an organic layer thereof was washed with sodium thiosulfate solution and saturated saline in this order. Then, magnesium sulfate was added to the organic layer, so that the moisture was removed. This suspending solution was filtered, so that a filtrate was obtained. The obtained filtrate was concentrated to provide a solid. The obtained solid was recrystallized with ethanol, whereby 3.1 g of a light-yellow solid of 9-iodine-lO-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 83 % (synthesis scheme (a-3)).
83%	With n-butyllithium; iodine; In tetrahydrofuran;	(iii) Synthesis of 9-iodo-10-phenylanthracene The following shows Synthesis Scheme (F-3) of 9-iodo-10-phenylanthracene. After 3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF) and cooled to -78 C., 7.5 mL (12.0 mmol) of n-BuLi (1.6 mol/L) was dropped through a dropping funnel into the reaction solution, and the mixture was stirred for one hour. Subsequently, a solution of 5 g (20.0 mmol) of iodine dissolved in 20 mL of THF was dropped, and the solution was further stirred at -78 C. for two hours. After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated and recrystallized with ethanol; thus, 3.1 g of a light-yellow solid of 9-iodo-10-phenylanthracene as a target matter was obtained with a yield of 83%.
83%		(3) Synthesis of 9-iodo-lO-phenylanthracene; After dissolving 3.33 g (10 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> in 80 mL of THF, the solution was cooled to -78 0C. Then, 7.5 mL (1.6 M, 12.0 mmol) of n-BuLi was dripped, and the mixture was stirred for one hour. Next, a solution of 5 g (20.0 EPO <DP n="61"/>mmo.l) of iodine in 20 mLof THF was dripped at -78 0C, and then the mixture was further stirred for 2 hours. After the reaction, an aqueous sodium thiosulfate solution was added to stop reaction. An organic layer was washed with an aqueous sodium thiosulfate solution and a saturated aqueous sodium chloride solution in this order. After washing, the organic layer was dried with magnesium sulfate and then filtered naturally. After concentrating the filtrate, the filtrate was recrystallized with ethanol, thereby obtaining 3.1 g of 9-iodo-lO-phenylanthracene as a light yellow solid (yield: 83 %). A synthesis scheme of 9-iodo-10-phenylanthracene from 9-bromo-lO-phenylarithracene is shown below.
83%		3.33 g (10 mmol) of 9-bromo-lO-phenylanthracene was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF), and cooled to -78 0C. Then, in a reaction solution thereof, 7.5 mL (12.0 mmol) of n-butyllithium (abbreviation: n-BuLi) (1.6 mol/L hexane solution) was dropped with a dropping funnel and then stirred for 1 hour. A solution in which 5 g (20.0 mmol) of iodine was dissolved in 20 mL of THF was dropped therein, and further stirred for 2 hours at -78 0C. After reaction, a sodium thiosulfate solution was added and stirred. An organic layer was washed with a sodium thiosulfate solution and saturated saline, and then dried with magnesium sulfate. A mixed solution was naturally filtered, a filtrate was concentrated, and then an obtained solid was recrystallized with ethanol. Then, 3.1 g of9-iodo-10-phenylanthracene that was a target substance and was a light yellow solid was obtained in a yield of 83 % (Synthesis Scheme (b-3)).

Reference： [1]Patent: US2008/81934,2008,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2006/104221,2006,A1 .Location in patent: Page/Page column 61
[3]Patent: WO2007/13537,2007,A1 .Location in patent: Page/Page column 95
[4]Patent: WO2007/7885,2007,A1 .Location in patent: Page/Page column 53-54
[5]Patent: US2007/96639,2007,A1 .Location in patent: Page/Page column 111
[6]Patent: US2007/149784,2007,A1 .Location in patent: Page/Page column 78
[7]Patent: WO2007/43354,2007,A1 .Location in patent: Page/Page column 115-116
[8]Patent: US2009/174321,2009,A1
[9]Patent: WO2009/81800,2009,A1 .Location in patent: Page/Page column 126
[10]Patent: US2010/1638,2010,A1
[11]Patent: WO2007/26626,2007,A1 .Location in patent: Page/Page column 59-60
[12]Patent: WO2007/29530,2007,A1 .Location in patent: Page/Page column 61
[13]Bulletin de la Societe Chimique de France,1937,vol. <5> 4,p. 1260,1261

3
[ 23674-20-6 ]
[ 602-55-1 ]
[ 84-65-1 ]
[ 86170-67-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 10% 3: 42%	With potassium phenolate In N,N-dimethyl-formamide at 153℃; for 41h;

Reference： [1]Rigaudy, J.; Seuleiman, A.M.; Cuong, Nguyen Kim [Tetrahedron, 1982, vol. 38, # 21, p. 3157 - 3162]

4
[ 23674-20-6 ]
[ 85199-06-0 ]
2-(9-phenylanthracen-10-yl)-p-xylene [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2002,vol. 106,p. 7512 - 7520

5
[ 858641-06-2 ]
[ 23674-20-6 ]
9-{N-[4-(carbazol-9-yl)phenyl]-N-phenylamino}-10-phenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 13h;	A synthetic scheme of YGAPhA is shown in (B-7). Into a 100 mL three-neck flask were added 2.0 g (6.0 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 2.4 g (7.2 mmol) of 4-(carbazol-9-yl)diphenylamine (abbreviation: YGA), 0.17 g (0.30 mmol) of bis(dibenzylideneacetone)palladium(0), and 2.9 g (30 mmol) of sodium-tert-butoxide, and the atmosphere in the flask was substituted by nitrogen. Thereafter, 20 mL of toluene and 0.61 g (0.30 mmol) of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to the mixture. This mixture was stirred at 80 C. for 13 hours. After the reaction, the mixture was washed with water. An aqueous layer was extracted with ethyl acetate, and the extracted solution was combined with an organic layer and dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated. A residue obtained was dissolved in toluene and this solution was filtered through Florisil, celite, and alumina by suction filtration. The filtrate was concentrated to obtain a solid. Recrystallization of the solid with chloroform and hexane gave 3.2 g of 9-{N-[4-(carbazol-9-yl)phenyl]-N-phenylamino}-10-phenylanthracene (abbreviation: YGAPhA), that is the object substance, as yellow powder in 91% yield. 1H NMR data of this compound is shown below. 1H NMR (300 MHz, CDCl3); delta=7.21-7.39 (m, 17H), 7.45-7.53 (m, 4H), 7.57-7.63 (m, 3H), 7.74-7.77 (m, 2H), 8.10-8.13 (m, 2H), 8.27-8.30 (m, 2H). The 1H NMR chart is shown in . Note that the range of 6.5 ppm to 8.5 ppm in is expanded and shown in

Reference： [1]Patent: US2008/86012,2008,A1 .Location in patent: Page/Page column 72-73

6
[ 894791-43-6 ]
[ 23674-20-6 ]
9-[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-10-phenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 3h;	Step 2]; Synthesis of PCAPhA A synthetic scheme of PCAPhA is shown in (B-3).; Into a 100 mL three-neck flask were added 501 mg (1.5 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 504 mg (1.5 mmol) of N,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA), and 500 mg (5.2 mmol) of sodium-tert-butoxide, and the atmosphere in the flask was substituted by nitrogen. Thereafter, 10 mL of toluene and 0.1 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to the mixture. This mixture was stirred under reduced atmosphere to be degassed. After degassing, 43 mg (0.075 mmol) of bis(dibenzylideneacetone)palladium(0) was added. This mixture was stirred at 80 C. for 3 hours under nitrogen. After the reaction, the mixture was added with about 20 mL of toluene and then washed with water. An aqueous layer was extracted with toluene, and the extracted solution was combined with an organic layer and washed with saturated saline. The organic layer was dried with magnesium sulfate, this mixture was naturally filtered, and the filtrate was concentrated. A solid obtained was purified by silica gel column chromatography (developing solvent; hexane:toluene=7:3). Recrystallization of the obtained solid with a mixed solvent of chloroform and hexane gave 514 mg of 9-[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-10-phenylanthracene (abbreviation: PCAPhA) as yellow powder in 67% yield.

Reference： [1]Patent: US2008/86012,2008,A1 .Location in patent: Page/Page column 68

7
[ 419536-33-7 ]
[ 23674-20-6 ]
CzPA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 90℃; for 4h;	[Step 3] Synthesis of 9-[4-(JV-carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA); A synthesis scheme of CzPA is shown in (B-5).; 1.44 g (4.32 mmol) of 9-bromo-lO-phenylanthracene, 1.49 g (5.19 mmol) of <strong>[419536-33-7]4-(carbazol-9-yl)phenylboronic acid</strong>, 38.0 mg (0.17 mmol) of palladium acetate(II), and 0.36 g (1.21 mmol) of tris(o-tolyl)phosphine were put into a 100-mL three-neck flask and nitrogen substitution was carried out. Then, 10 mL of ethylene glycol dimethyl <n="79"/>ether (DME) and 6.5 mL (13.0 mmol) of a sodium carbonate aqueous solution (2.0 mol/L) were added and the solution was stirred at 90 0C for 4 hours. After that, the reaction mixture was subjected to suction filtration to collect a precipitated solid. The obtained solid was dissolved into chloroform, and the solution was subjected to suction filtration through Florisil, celite, and then alumina. The filtrate was condensed to obtain a solid, and the solid was recrystallized with a mixture solvent of chloroform and hexane, whereby 1.81 g of a light yellow powdery solid that was a target matter was obtained with the yield of 85 %. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was 9-[4-(JV-carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA). [0229]1H NMR data of CzPA is shown below. 1H NMR (300MHz, CDCl3) ; delta = 8.22(d, J = 7.8Hz, 2H), 7.86-7.82 (m, 3H), 7.61-7.36 (m, 20H). The 1K NMR chart is shown in FIGS. 1OA and 1OB. It is to be noted that the range of 6.5 ppm to 8.5 ppm in FIG 10A, which is expanded, is shown in FIG 1OB.

Reference： [1]Patent: WO2008/26614,2008,A1 .Location in patent: Page/Page column 77-78

8
[ 877176-68-6 ]
[ 23674-20-6 ]
2,3-bis[4-(9-phenyl-10-anthryl)phenyl]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 17h;	4.0 g (12 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 2.0 g (5.4 mmol) of 4,4'-(quinoxaline-2,3-diyl)diphenyl boronic acid that was synthesized in Embodiment 1, 0.024 g (0.11 mmol) of palladium(II) acetate, and 0.23 g (0.76 mmol) of tri(ortho-tolyl)phosphine were put into a 100 mL three-neck flask, and nitrogen substitution in the flask was carried out. Then, 30 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 8 mL (16 mmol) of a potassium carbonate aqueous solution (2.0 mol/L) were added to this mixture. This mixture was refluxed under a nitrogen-gas substitution stream at 80 C. for 17 hours. After completion of a reaction, a precipitate in the reaction mixture was collected by suction filtration. An obtained solid was dissolved in chloroform, and this solution was subjected to suction filtration through Florisil, celite, and alumina. When a filtrate was concentrated and an obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 2.4 g of a light yellow, powdery solid that was a target matter, was obtained with the yield of 55%. By a nuclear magnetic resonance method (NMR), it was confirmed that this compound was 2,3-bis[4-(9-phenyl-10-anthryl)phenyl]quinoxaline (abbreviation: PAPQ). When 2.3 g of the obtained 2,3-bis[4-(9-phenyl-10-anthryl)phenyl]quinoxaline (abbreviation: PAPQ) was subjected to sublimation purification by heating it to 360 C. under a condition of a pressure of 7.8 Pa and an argon flow rate of 3.0 mL/min, 1.7 g was collected, and the collection rate was 71%. The analysis result of PAPQ by a proton nuclear magnetic resonance method (1H NMR) was as follows: 1H NMR (300 MHz, CDCl3): delta=7.03-7.07 (m, 1H), 7.16-7.21 (m, 5H), 7.24-7.30 (m, 4H), 7.47-7.50 (m, 4H), 7.55-7.63 (m, 10H), 7.67-7.70 (m, 4H), 7.75-7.78 (m, 4H), 7.88-7.95 (m, 6H). In addition, a 1H NMR chart is shown in each of FIGS. 15A and 15B. Note that FIG. 15B is a chart showing an enlargement of FIG. 15A in the range of 6.0 ppm to 9.0 ppm.

Reference： [1]Patent: US2008/91012,2008,A1 .Location in patent: Page/Page column 33

9
[ 474687-82-6 ]
[ 23674-20-6 ]
2-(10-phenylanthracen-9-yl)bispiro(9,10-dihydroanthracene-9,7′-7′H-fluorene-10,7″-7″H-fluorene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 60℃; for 12h;	To a suspension of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> (0.3 g, 1.00 mmol), Chemical Compound 8 (0.52 g, 1.00 mmol), and potassium phosphate (0.42 g, 2.00 mmol)) in DMF (10 ml) was added tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) under nitrogen. After the reaction mixture had been stirred at 60 C. for 12 hours, it was cooled to room temperature. Ethanol (20 ml) was added to the mixture, and then the mixture was stirred for 30 minutes at room temperature. The precipitate was filtered off with suction, washed with water, ethanol, and acetone, and dried under vacuum. Then it was dissolved in chloroform (150 ml) and filtered through a short column packed with silica gel. After removal of solvent, the crude product was purified by crystallizing from ethanol to give Chemical Compound 109 (0.26 g, 35%): mp 448 C.; 1H NMR (400 MHz, N-methylpyrrolidine-d9) delta 8.26 (d, J=7 Hz, 2H), 8.00 (dd, J=3.0, 7.0 Hz, 2H), 7.62-7.54 (m, 9H), 7.48-7.38 (m,9H), 7.35-7.29 (m, 5H), 7.20-7.16 (m, 2H), 7.10 (dd, J=2.0, 8.0 Hz, 1H), 6.95-6.90 (m, 2H), 6.66 (d, J=8.0 Hz, 1H), 6.49 (d, J=2.0 Hz, 1H), 6.42-6.39 (m, 2H); MS (M+) calculated for C58H36 732. found 732. analysis calculated for C58H36: C, 95.05; H, 4.95. Found: C, 95.07; H, 4.88.

Reference： [1]Patent: US6998487,2006,B2 .Location in patent: Page/Page column 49

10
[ 523-27-3 ]
[ 98-80-6 ]
[ 23674-20-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 48h;Heating / reflux;	SYNTHESIS EXAMPLE 1; Synthesis of Intermediate A; An intermediate A was synthesized according to Reaction Scheme 1 below: 9,10-dibromoanthracene (4.00 g, 11.90 mmol) and phenylboronic acid (1.60 g, 13.12 mmol) were dissolved in toluene (100 ml), and Pd(PPh3)4 (0.68 g, 0.59 mmol) and 2M K2CO3 (24 ml) were gradually dropwise added thereto. The reaction mixture was refluxed for 48 hours and cooled to room temperature. Then, a solvent was removed under a reduced pressure, and the residue was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and an organic layer was collected and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography using as an eluant, a solution of chloroform and hexane (1:1 v/v) to give 2.27 g (yield: 57%) of a compound of Formula 1b. The compound of Formula 1b (2.20 g, 6.60 mmol) was dissolved in tetrahydrofuran (100 ml), and n-butyllithium (4.6 ml, 7.36 mmol, 1.6 M solution) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.48 ml, 7.25 mmol) were gradually dropwise added thereto at -78 C. The reaction mixture was gradually heated to room temperature and incubated at room temperature for 15 hours. Then, water (H2O) (50 ml) was added to the reaction solution so that the reaction was terminated, and the resultant solution was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and an organic layer was collected and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography using as an eluant, a solution of chloroform and hexane (1:1 v/v) to give 1.53 g (yield: 61%) of a compound of Formula 1c. A compound of Formula 1d (1.80 g, yield: 61%) was synthesized in the same manner as in the synthesis of the compound of Formula 1b except that 3-bromoiodobenzene was used instead of 9,10-dibromoanthracene, and the compound of Formula 1c (2.75 g, 7.23 mmol) was used instead of phenylboronic acid. The intermediate A (1.70 g, yield: 56%) was synthesized in the same manner as in the synthesis of the compound of Formula 1c except that the compound of Formula 1d (2.70 g, 6.60 mmol) was used instead of the compound of Formula 1b.
57%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene;Reflux;	Synthesis Example 1 Synthesis of Intermediate AAn intermediate A was synthesized according to Reaction Scheme 1 below: 9,10-dibromoanthracene (4.00 g, 11.90 mmol) and phenylboronic acid (1.60 g, 13.12 mmol) were dissolved in toluene (100 ml), and Pd(PPh3)4 (0.68 g, 0.59 mmol) and 2M K2CO3 (24 ml) were gradually dropwise added thereto. The reaction mixture was refluxed for 48 hours and cooled to room temperature. The solvent was removed under reduced pressure, and the residue was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and the organic layer was collected and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography to yield 2.27 g (57%) of the intermediate A.
45%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 100℃; for 12h;Inert atmosphere;	Synthesis of 9-bromo-10-phenylanthracene A mixture of 40 g (119 mmol) of 9,10-dibromoanthracene, 16 g (131 mmol) of phenylboronic acid, 1.38 g (1.2 mmol) of Pd(PPh3)4, 120 ml of 2M Na2CO3, 150 ml of EtOH and 450 ml toluene was degassed and placed under nitrogen, and then heated at 100 C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica to give product (17.8 g, 53.6 mmol, 45%) as a yellow solid.

	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 3h;	Synthesis (C3-1); 2.2 g of commercially available phenylboronic acid and 6 g of 9,10-dibromoanthracene were dissolved in 100 ml of dimethoxyethane and were heated to 80 C. 50 ml of distilled water and 10 g of sodium carbonate were added thereto. Also, 0.5 g of tetrakis-triphenylphosphine palladium(0) was added thereto.After 3 hours, extraction with toluene was carried out in a separatory funnel and purification using silica gel (SiO2, 500 g) was carried out.As a result, 4 g of pale yellow crystals (9-bromo-10-phenylanthracene) was obtained.
4 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 80℃; for 3h;	g 2.2 g of 9, 10 - 100 ml of phenyl boronic acid with commercially available [jiburomoantorasen[jiburomoantorasen] dissolved in dimethoxyethane, 80 C heated. 50 ml distilled water and sodium carbonate 10 g was placed therein. Further thereto was placed 0.5 g (0) tetrakistriphenylphosphine. 3 hours after the separatory funnel by extraction with toluene, silica (SiO2 500 g) was purified. Therefore, yellowish white crystals (9 - bromo - phenyl -10 - anthracene) 4 g was obtained
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 2h;Reflux; Inert atmosphere;	A mixture of compound 4 (33.4 g, 100 mmol), phenylboronic acid (12.2 g, 100 mmol)(5.78 g, 5 mmol) and potassium carbonate (41.4 g, 300 mmol) were added to toluene (500 ml), refluxed under nitrogen for 2 hours, cooled to room temperature and used directly in The next step.
94%Chromat.	With C30H34Cl4N4Pd2; potassium carbonate; In methanol; at 60℃; for 24h;	General procedure: [1] Reaction conditions: 0.50 mmol of halogenated aromatics, 0.60 mmol of phenylboronic acid, 1.0 mmol of K2CO3, prepared in Example 2. The prepared nitrogen heterocyclic biscarbene metal complex 0.2 mol%, solvent 5 mL, PEG400 (0.1 mL), 60 C.
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 25h;Inert atmosphere; Reflux;	9,10-dibromoanthracene (5 mmol), phenyl boronic acid (5 mmol), Pd(PPh3)4 (0.5 mmol), Na2CO3 (2.0 M) aqueous solution (15 mL), ethanol (10 mL), and toluene (30 mL) were added to a flask and mixed. A gas was removed from the mixture, and the mixture was refluxed in a nitrogen atmosphere for 25 hours. After the mixture was cooled, a solvent was evaporated therefrom in a vacuum, and a product was extracted therefrom by using dichloromethane. CH2Cl2 solution was washed with water and dried by using MgSO4.

Reference： [1]Patent: US2008/111478,2008,A1 .Location in patent: Page/Page column 10-11
[2]Patent: US7718278,2010,B2 .Location in patent: Page/Page column 18-19
[3]Patent: US2016/285004,2016,A1 .Location in patent: Paragraph 0021; 0022
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 3606 - 3610
Angew. Chem.,2016,vol. 128,p. 3670 - 3674,5
[5]Journal of Materials Chemistry,2010,vol. 20,p. 3186 - 3194
[6]Patent: US2012/267615,2012,A1 .Location in patent: Page/Page column 50
[7]Patent: JP6145989,2017,B2 .Location in patent: Paragraph 0148
[8]Patent: CN107216347,2017,A .Location in patent: Paragraph 0046; 0047; 0055; 0056
[9]Patent: CN107880079,2018,A .Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040; 0041
[10]Patent: US2020/75869,2020,A1 .Location in patent: Paragraph 0331-0332; 0335-0336

11
[ 61676-62-8 ]
[ 23674-20-6 ]
[ 460347-59-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃; for 12h;	9-Bromo-10 benzoquinone boronate: 1.40 g of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 1.34 g of isopropoxyborate, 0.42 g of n-butyllithium (added at -78 C),30 mL of THF was added to the reaction flask, and the system was evacuated and stirred at room temperature for 12 hours.After the reaction, extraction, column chromatography (eluent n-hexane / dichloromethane = 1:1),Recrystallization (n-hexane/toluene = 3:1) gave the product 9-phenylanthracene-10-borate. The yield was 77%.
77%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃; for 12h;	9-bromo-10 benzoquinone2.80g, 2.67g of isopropoxyborate, 0.81g of n-butyllithium (added at -78 C),56 mL of THF was added to the reaction flask, and then the system was evacuated and stirred at room temperature for 12 hours.After completion of the reaction, toluene extraction, rotary distillation, column chromatography (eluent n-hexane / dichloromethane = 1:1), recrystallization (n-hexane / toluene = 3:1) affords 9-phenylindole-10 boric acid The ester product was 77%.
62%		<strong>[23674-20-6]10-phenyl-9-bromoanthracene</strong> (1.51 g, 4.54 mmol) was provided in a 50 ml two-neck bottle. After installing a dropping funnel and a three-way valve, and purged with argon for three times, anhydrous THF (22.5 ml) was added into the bottle. The mixture was stayed at -78 C., and then n-BuLi (3.3 ml, 5.28 mmol) was added slowly. After stirring for 1 hour at -78 C. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 ml, 4.9 mmol) was added, and the mixture was returned to room temperature and stirred for 4 hours. 2M HCl (2 ml) was added to quench reaction, and THF was removed. The solution was extracted with trichloromethane, deionized water and saturated NaCl solution, respectively, and the organic layer was dried with anhydrous MgSO4. The solution was purified through by column chromatography with n-hexane/DCM=2-1 (gradually changed) as eluent, and re-crystalized with DCM and n-hexane to obtain compound 3 (PhBorAn, Chemical Formula (3), 1.07 g, yield: 62%) as a white solid. The foregoing reaction is as shown in the Reaction Formula (6). Spectral data as follow: 1H NMR (400 MHz, CDCl3) delta 8.42 (d, J=8.8 Hz, 2H), 7.62 (d, J=8.8 Hz, 2H), 7.57-7.51 (m, 3H) 7.48-7.43 (m, 2H), 7.39-7.37 (m, 2H), 7.32-7.28 (m, 2H); 13C NMR (100 Mhz, CDCl3) delta 139.56, 139.12, 135.36, 131.07, 130.00, 128.37, 128.28, 127.38, 125.40, 124.80, 84.47. HRMS (FAB) m/z calcd for C26H25BO2 380.1948 obsd. 380.1946. Anal. Calcd for C26H25BO2: C, 82.12; H, 6.63. Found: C, 81.63; H, 6.08.

61%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃; for 15h;	SYNTHESIS EXAMPLE 1; Synthesis of Intermediate A; An intermediate A was synthesized according to Reaction Scheme 1 below: 9,10-dibromoanthracene (4.00 g, 11.90 mmol) and phenylboronic acid (1.60 g, 13.12 mmol) were dissolved in toluene (100 ml), and Pd(PPh3)4 (0.68 g, 0.59 mmol) and 2M K2CO3 (24 ml) were gradually dropwise added thereto. The reaction mixture was refluxed for 48 hours and cooled to room temperature. Then, a solvent was removed under a reduced pressure, and the residue was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and an organic layer was collected and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography using as an eluant, a solution of chloroform and hexane (1:1 v/v) to give 2.27 g (yield: 57%) of a compound of Formula 1b. The compound of Formula 1b (2.20 g, 6.60 mmol) was dissolved in tetrahydrofuran (100 ml), and n-butyllithium (4.6 ml, 7.36 mmol, 1.6 M solution) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.48 ml, 7.25 mmol) were gradually dropwise added thereto at -78 C. The reaction mixture was gradually heated to room temperature and incubated at room temperature for 15 hours. Then, water (H2O) (50 ml) was added to the reaction solution so that the reaction was terminated, and the resultant solution was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and an organic layer was collected and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography using as an eluant, a solution of chloroform and hexane (1:1 v/v) to give 1.53 g (yield: 61%) of a compound of Formula 1c. A compound of Formula 1d (1.80 g, yield: 61%) was synthesized in the same manner as in the synthesis of the compound of Formula 1b except that 3-bromoiodobenzene was used instead of 9,10-dibromoanthracene, and the compound of Formula 1c (2.75 g, 7.23 mmol) was used instead of phenylboronic acid. The intermediate A (1.70 g, yield: 56%) was synthesized in the same manner as in the synthesis of the compound of Formula 1c except that the compound of Formula 1d (2.70 g, 6.60 mmol) was used instead of the compound of Formula 1b.
61%	With n-butyllithium; In tetrahydrofuran; at -78 - 20℃;	Synthesis Example 3Synthesis of Intermediate CAn intermediate C was synthesized according to Reaction Scheme 2 below: The intermediate A was synthesized according to Synthesis Example 1. The intermediate A (2.20 g, 6.60 mmol) was dissolved in tetrahydrofuran (100 ml), and n-butyllithium (4.6 ml, 7.36 mmol, 1.6 M solution) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.48 ml, 7.25 mmol) were gradually dropwise added thereto at -78 C. The reaction mixture was heated to room temperature and incubated at room temperature for 15 hours. The reaction was terminated by the addition of water (H2O) (50 ml), and the resultant solution was extracted with chloroform. The extracted solution was twice washed with a supersaturated sodium chloride solution and water (H2O), and the organic layer was collected and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain a crude product, and the crude product was purified by silica gel column chromatography to yield 1.53 g (61%) of the compound of Formula 1b. The intermediate C (1.80 g, yield: 61%) was synthesized according to Synthesis Example 1 except that 3-bromoiodobenzene was used instead of 9,10-dibromoanthracene, and the compound of Formula 1b (2.75 g, 7.23 mmol) was used instead of phenylboronic acid.
60%	With n-butyllithium; In tetrahydrofuran; at 20℃; for 8h;	(3) 9 - Bromo -10 benzene anthracene boric acid ester: will be 9 - bromo -10 benzene anthracene 1.40 g, [...] ester 1.34 g, n-BuLi 0.42 g (in -78 C adding), THF 30 ml is added to the reaction bottle, vacuum to the systems, stirring at room temperature 8 hours. After the reaction, extraction, column chromatography (eluent hexane/dichloromethane=1:1), recrystallized (hexane/toluene=3:1) to obtain the product 9 - benzene anthracene -10 borate. Yield 60%.
	With n-butyllithium;	3rd step: 4,4,5,5-tetramethyl-2-(10-phenylanthracen-9-yl)-1,3,2-dioxaborolane <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> (2.3 g, 6.9 mmol, 1.0 eq) was dissolved under argon atmosphere in THF and cooled to -80 C. n-butyl lithium (1.6 M in THF, 5.5 mL, 13.8 mmol, 2.0 eq) was added dropwise and the mixture was stirred for 30 min at -80 C. Then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.22 mL, 3.86 g, 20.7 mmol, 3.0 eq) was added dropwise, and the mixture was allowed to warm to room temperature (without removing the cooling bath). The reaction was quenched by adding MeOH (1 mL), and after 10 min of stiffing, the solvent was removed under reduced pressure. The crude product was dissolved in chloroform (120 mL) and extracted with water (3*30 mL). The organic layer was decanted, dried over magnesium sulfate, and evaporated to dryness. 20 mL hexane were added to the residue, and the mixture was treated in an ultrasound bath for about 15 min. Finally, the precipitate was filtered off. GC-MS purity: 97.65%

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 17320 - 17333
[2]Patent: CN108383693,2018,A .Location in patent: Paragraph 0050; 0053; 0055; 0056; 0057; 0058
[3]Patent: CN109265310,2019,A .Location in patent: Paragraph 0044; 0055; 0057; 0061; 0062; 0063; 0064
[4]Patent: US2020/28088,2020,A1 .Location in patent: Paragraph 0083-0084
[5]Patent: US2008/111478,2008,A1 .Location in patent: Page/Page column 10-11
[6]Patent: US7718278,2010,B2 .Location in patent: Page/Page column 20-21
[7]Patent: CN109678645,2019,A .Location in patent: Paragraph 0042; 0052; 0055
[8]Journal of Materials Chemistry,2010,vol. 20,p. 3186 - 3194
[9]Patent: US2018/114914,2018,A1

12
[ 1093856-18-8 ]
[ 23674-20-6 ]
[ 602-55-1 ]
[ 1093856-15-5 ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 90℃; for 60h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Moorthy, Jarugu Narasimha; Venkatakrishnan, Parthasarathy; Natarajan, Palani; Huang, Duo-Fong; Chow, Tahsin J. [Journal of the American Chemical Society, 2008, vol. 130, # 51, p. 17320 - 17333]

13
[ 1065657-51-3 ]
[ 23674-20-6 ]
[ 1196690-42-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 6h;Inert atmosphere;	[Step 3: Synthesis of 2-[4-(10-phenyl-9-anthryl)phenyl]benzoxazole] A synthesis scheme of 2-[4-(10-phenyl-9-anthryl)phenyl]benzoxazole is shown in (B-6). In a 50 mL three-neck flask, 1.0 g (3.0 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 0.72 g (3.0 mmol) of 4-(benzoxazol-2-yl)phenylboronic acid, 0.10 g (0.32 mmol) of tri(ortho-tolyl)phosphine, 20 mL of ethylene glycol dimethyl ether (DME), and 3.0 mL (6.0 mmol) of a 2.0 M potassium carbonate solution were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 14 mg (0.062 mmol) of palladium(II) acetate was added, and the mixture was stirred under nitrogen stream at 80 C. for 6 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give an oily substance. The oily substance was purified by silica gel column chromatography (toluene:hexane=2:1) and recrystallized with toluene/methanol, giving 1.1 g of the target pale yellow powder in a yield of 81%. Then, 1.1 g of the target substance was subjected to sublimation purification at 230 C. under argon stream (flow rate: 3.0 mL/min) and a pressure of 10 Pa for 17 hours; thus, 0.96 g of the target substance was recovered in a yield of 69%. This compound was measured by nuclear magnetic resonance (NMR) spectrometry and identified as 2-[4-(10-phenyl-9-anthryl)phenyl]benzoxazole (abbrev.: PABOx). The 1H NMR data and the 13C NMR data are shown below. 1H NMR (300 MHz, CDCl3): delta (ppm)=7.32-7.43 (m, 6H), 7.47-7.50 (m, 2H), 7.58-7.73 (m, 100H), 7.83-7.87 (m, 1H), 8.51 (d, J=8.1 Hz, 2H). 13C NMR (75 MHz, CDCl3): delta (ppm)=110.67, 120.12, 124.67, 125.10, 125.22, 125.38, 126.43, 126.52, 127.11, 127.55, 127.72, 128.43, 129.61, 129.84, 131.25, 132.06, 135.76, 137.70, 138.87, 142.23, 142.82, 150.88, 163.01.

Reference： [1]Patent: US2009/286985,2009,A1 .Location in patent: Page/Page column 63-64

14
(4-(3-phenyl-9H-carbazol-9-yl)phenyl)boronic acid [ No CAS ]
[ 23674-20-6 ]
[ 1218786-27-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium or potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 80℃; for 9h;Inert atmosphere;	In a 100 mL three neck flask were put 1.4 g (4.1 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> and 1.5 g (4.1 mmol) of 4-(3-phenyl-9H-carbazol-9-yl)phenylboronic acid. The atmosphere in the flask was replaced with nitrogen. Then, to this mixture were added 50 mL of toluene and 5.0 mL of an aqueous potassium carbonate solution (2.0 mol/L). The mixture was stirred to be degassed while the pressure was reduced. To this mixture was added 0.24 g (0.20 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred under a nitrogen stream at 80 C. for 9 hours.After being stirred, this mixture was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with toluene. The extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, followed by gravity filtration of this mixture. A solid obtained by concentration of the resulting filtrate was dissolved in about 10 mL of toluene. This solution was suction filtered through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the resulting filtrate was purified by silica gel column chromatography (the developing solvent was a mixed solvent of a 5:1 ratio of hexane to toluene) to give a light yellow oily substance.This oily substance was recrystallized with a mixed solvent of toluene and hexane to give the desired substance as 1.9 g of a light yellow powder in a yield of 83%. As in Example of Production of CzPAP, by a nuclear magnetic resonance (NMR) method, this compound was confirmed to be 3-phenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPAP) which was the desired compound.

Reference： [1]Patent: US2010/76201,2010,A1 .Location in patent: Page/Page column 32

15
potassium phosphate [ No CAS ]
[ 23674-20-6 ]
[ 61921-39-9 ]
[ 6163-58-2 ]
[ 1087346-88-0 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 1,4-dioxane; water; toluene;	a) 4-(9-Phenylanthracen-10-yl)benz[a]anthracene 3 g (9.8 mmol) of tri-o-tolylphosphine and then 391 mg (1.7 mmol) of palladium(II) acetate are added to a well-stirred suspension of 20 g (60 mmol) of 9-bromo-10-phenylanthracene, 19.8 g (73 mmol) of 4-bromo-benz[a]-anthracene and 19 g (89 mmol) of tripotassium phosphate in a mixture of 250 ml of toluene, 50 ml of dioxane and 250 ml of water, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol and finally dried. Yield: 34 g (71 mmol), 97%.

Reference： [1]Patent: US2010/187505,2010,A1

16
[ 1158844-78-0 ]
[ 23674-20-6 ]
[ 1158844-47-3 ]

Yield	Reaction Conditions	Operation in experiment
52%	With Aliquat 336; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 4h;	Compound (128) (2.0 g, 3.1 mmol), Compound (202) (2.6 g, 7.8 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.4 g, 0.3 mmol), aqueous 1.0 M potassium carbonate solution (16 mL), Aliquat 336 (0.34 mL, 0.6 mmol) and toluene (40 mL) were mixed together, and the mixture was stirred at 100 C. for 6 hours. After cooling to ambient temperature, the organic layer was extracted with dichloromethane (250 mL), and the extract was washed with distilled water (200 mL). Drying over magnesium sulfate and distillation under reduced pressure gave solid, which was then recrystallized from acetone (30 mL), ethyl acetate (30 mL), and tetrahydrofuran (20 mL) to obtain Compound (321) (0.8 g, 0.9 mmol, yield: 29%).1H NMR (200 MHz, CDCl3): delta=7.16-7.22 (m, 6H), 7.31-7.36 (m, 14H), 7.46-7.50 (m, 4H), 7.53-7.55 (m, 4H), 7.59-7.61 (m, 2H), 7.65-7.69 (m, 8H), 7.71-7.73 (m, 2H), 7.77 (d, 2H), 7.90-7.92 (d, 2H)MS/FAB: 896 (found), 897.10 (calculated).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 35

17
[ 1158844-81-5 ]
[ 23674-20-6 ]
[ 1158844-48-4 ]

Yield	Reaction Conditions	Operation in experiment
36%	With Aliquat 336; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 6h;	Compound (120) (3.0 g, 4.5 mmol), Compound (202) (3.8 g, 11.4 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.5 g, 0.5 mmol), aqueous 1.0 M potassium carbonate solution (22 mL), Aliquat 336 (0.5 mL, 0.9 mmol) and toluene (60 mL) were mixed together, and the mixture was stirred at 100 C. for 6 hours and cooled to 25 C. The organic layer was extracted with dichloromethane (200 mL), and the extract was washed with distilled water (200 mL). Drying over magnesium sulfate and distillation under reduced pressure gave solid, which was then recrystallized from acetone (50 mL), ethyl acetate (50 mL) and tetrahydrofuran (20 mL) to obtain Compound (324) (1.5 g, 1.6 mmol, yield: 36%).1H NMR (200 MHz, CDCl3): delta=2.35 (s, 3H), 6.92-6.94 (d, 4H), 7.07-7.14 (m, 5H), 7.21-7.23 (m, 2H), 7.30-7.36 (m, 12H), 7.46-7.49 (m, 4H), 7.53-7.55 (m, 4H), 7.59-7.61 (m, 2H), 7.65-7.69 (m, 8H), 7.77 (d, 2H), 7.90-7.92 (d, 2H)MS/FAB: 913.2 (found), 913.15 (calculated).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 36

18
[ 1158844-84-8 ]
[ 23674-20-6 ]
[ 1158844-49-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With Aliquat 336; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 4h;	Compound (142) (3.7 g, 5.2 mmol), Compound (202) (5.2 g, 15.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.6 g, 0.5 mmol), aqueous 1.0 M potassium carbonate solution (26 mL), Aliquat 336 (0.6 mL, 1.0 mmol) and toluene (80 mL) were mixed together, and the mixture was stirred at 100 C. for 4 hours and cooled to ambient temperature. The reaction mixture was extracted with dichloromethane (700 mL), and the extract was washed with distilled water (500 mL). Drying over) magnesium sulfate and distillation under reduced pressure gave solid, which was then recrystallized from acetone (100 mL), ethyl acetate (50 mL) and tetrahydrofuran (30 mL) to obtain Compound (325) (2.7 g, 2.8 mmol, yield: 54%).1H NMR (CDCl3, 200 MHz): delta=7.04-7.08 (m, 6H), 7.15 (t, 4H), 7.20 (t, 2H), 7.30 (t, 12H), 7.45-7.55 (m, 12H), 7.60-7.69 (m, 10H), 7.79 (d, 2H), 7.89 (d, 2H)MS/FAB: 974.39 (found), 975.22 (calculated).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 38

19
[ 1158844-51-9 ]
[ 23674-20-6 ]
[ 1158844-32-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With Aliquat 336; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 4h;	In toluene (80 mL), dissolved were Compound (104) (2.7 g, 5.2 mmol), Compound (202) (5.2 g, 15.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.6 g, 0.5 mmol), aqueous 1.0 M potassium carbonate solution (26 mL) and Aliquat 336 (0.6 mL, 1 mmol). After stirring at 100 C. for 4 hours, the mixture was cooled to 25 C. The organic layer was extracted with dichloromethane (300 mL) and washed with distilled water (260 mL). Drying over magnesium sulfate, distillation under reduced pressure, recrystallization from acetone (50 mL) and tetrahydrofuran (50 mL) and drying under reduced pressure gave Compound (301) (1.6 g, 2.6 mmol, yield: 50%).1H NMR (200 MHz, CDCl3): delta=1.65 (s, 6H), 7.27 (m, 2H), 7.36-7.44 (m, 12H), 7.54-7.58 (m, 4H), 7.60-7.64 (d, 4H), 7.67 (m, 2H), 7.70-7.74 (m, 8H), 7.84 (d, 2H), 7.90-7.93 (m, 2H)MS/FAB: 824 (found), 825.04 (calculated).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 11

20
[ 1033893-89-8 ]
[ 23674-20-6 ]
C₆₇H₄₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With Aliquat 336; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 120℃; for 6h;	A reaction vessel was charged with Compound (136) (5.0 g, 8.3 mmol), Compound (202) (8.3 g, 24.9 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.96 g, 0.83 5 mmol), Aliquat 336 (0.4 mL, 0.83 mmol) and toluene (100 mL), and aqueous 2 M potassium carbonate solution (30 mL, 66 mmol) was added thereto. After stirring at 120 C. under reflux for 6 hours, the mixture was neutralized by using saturated aqueous ammonium chloride solution (100 mL), and the solid was filtered under reduced pressure. The dried solid was recrystallized from methanol (200 mL). Recrystallization from N,N-dimethylformamide (10 mL) gave Compound (310) (4.5 g, 5.3 mmol, yield: 64%).1H NMR (CDCl3, 200 MHz): delta=1.65 (s, 6H), 7.30 (t, 2H), 7.35 (m, 12H), 7.45 (dd, 4H), 7.54 (dd, 8H), 7.60 (d, 12H), 7.65 (m, 8H), 7.71 (d, 2H), 7.92 (dd, 2H)MS/FAB: 851.36 (found), 851.08 (calculated).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 20

21
[ 121-43-7 ]
[ 23674-20-6 ]
10-phenylanthracene-9-boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		10 L 4-neck round bottom flask intermediate 1-d 280g (0.84 mol) dissolved in 3000 mL of THF there by maintaining the temperature at -78C. 1.6 M n-BuLi 630 mL it was added dropwise slowly for 2 hours after stirring at the same temperature trimethylborate was added dropwise. Raise the temperature to room temperature, it was stirred for 12 hours. When complete the reaction 2N HCl was added. The organic layer was separated after neutralization was recrystallized from toluene to intermediate 1-e (228 g, 91%) was obtained.
91%		In a 10-L 4-neck, round-bottom flask, Intermediate 4-d (280 g, 0.84 mol) and THF (3000 mL) were placed and maintained at -78 C. 1.6M n-BuLi (630 mL) was slowly added to the solution which was then stirred for 2 hrs. At the same temperature, B(OMe)3 was dropwise added. The temperature was elevated to room temperature before stirring for 12 hrs. After completion of the reaction, 2N HCl was added. The organic layer was separated, neutralized, and recrystallized in toluene to afford Intermediate 4-e (228 g, 91%).
91%		280 g (0.84 mol) of Intermediate 1-d and 3000 mL of THF were added to a 10 L four neck round bottom flask and then maintained at a temperature of -78 C. 630 mL of 1.6 M n-butyllithium (n-BuLi) was slowly added thereto in a dropwise-manner, agitated for 2 hours, and then B(OMe)3 was added thereto in a drop-wise manner at the same (substantially the same) temperature. The temperature thereof was increased to room temperature and then agitated for 12 hours. After agitating for 12 hours (or after completing the reaction), 2 N HCl was added thereto. An organic layer was separated therefrom, neutralized, and then recrystallized with toluene to obtain Intermediate 1-e (228 g, 91%).

76.7%		<strong>[23674-20-6]9-phenyl-10-bromo-anthracene</strong> (13.4 g, 40 mmol) was dissolved in 110 mL THF. In the cooling state up to -78 was put in the n-BuLi (30 mL) slowly. At the end of the addition and then stirred for about 1 hour at -78 trimethyl borate (5.9 g, 56 mmol)It was put. After 1 hour stirring at -78 stirred at room temperature for about two hours and put in a 2 N HCl was adjusted to acidic. The solvent was then extracted with EA and obtained with hexane to give the 9-phenyl-10-anthracene boronic acid 9.2 g (yield 76.7%).
76.7%		In a round bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C. After the addition, the mixture was stirred at -78 C for about 1 hour, and trimethyl borate (11.8 g, 112 mmol) was added thereto. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid solution was added to adjust acidity. Crystals were extracted with hexane, followed by extraction with EA, to obtain 18.4 g (yield 76.7%) of 9-phenyl-10-anthraceneboronic acid.
71%		<Preparation Example 2-1> Preparation of the following Compound B-2 Compound B-1 (5.96 g, 17.9 mmol) was dissolved in tetrahydrofuran (100 mL), the temperature was decreased to -78C, and then 1.7 M tertiary-butyllithium (t-BuLi) (10.6 mL, 17.9 mmol) was slowly added thereto. The resulting mixture was stirred at the same temperature for 1 hour, trimethyl borate (B (OCH3)3) (3.72g, 35.8 mmol) was added thereto, and then the resulting mixture was stirred for 3 hours while slowly increasing the temperature to normal temperature. 2 N hydrochloric acid aqueous solution (30 mL) was added to the reaction mixture, and stirred at normal temperature for 1.5 hours. The produced precipitate was filtered and washed sequentially with water and ethyl ether, and then vacuum-dried. After drying, the precipitate was dispersed in ethyl ether, and the resulting mixture was stirred for 2 hours, filtered, and dried to prepare Compound B-2 (3.79 g, 71%). MS: [M+H] + = 299
69%		Intermediate 12-b (12.0 g, 36 mmol) was dissolved in 100 mL of tetrahydrofuran. After cooling to -78 C. under a nitrogen atmosphere, n-butyllithium (24.76 mL, 40 mmol) was slowly added dropwise for 30 min. The mixture was stirred at the same temperature for 1 h. To the mixture was added dropwise trimethyl borate (4.5 g, 43 mmol) at the same temperature. The resulting mixture was stirred at room temperature overnight. The reaction solution was acidified by dropwise addition of 2 N hydrochloric acid. After 1 h stirring, the mixture was extracted with ethyl acetate and recrystallized from hexane, affording 7.5 g (yield 69%) of Intermediate 12-c.
		Preparation of Compound (261); Under nitrogen atmosphere, Compound (260) (9.9 g, 29.8 mmol) was dissolved in tetrahydrofuran (200 mL), and the solution was chilled to -78 C. To the solution, slowly added dropwise was n-butyl lithium (n-BuLi, 2.5M in hexane) (15.5 mL, 38.7 mmol). After 30 minutes, trimethylborate (6.8 mL, 59.6 mmol) was added thereto, and the resultant mixture was slowly warmed to room temperature. After stirring at the same temperature for one day, aqueous 1N hydrochloric acid solution (100 mL) was added. The mixture was stirred for 30 minutes, and extracted from water (200 mL) and dichloromethane (200 mL). The extract was dried under reduced pressure and recrystallized from ethyl acetate (20 mL) and hexane (300 mL) to obtain the objective compound (261) (7.1 g, 23.8 mmol).
		250ml round bottom flask was put in the Intermediate b-1> (12.0g, 36mmol) was dissolved into 100ml of tetrahydrofuran. The reaction solution was cooled road -78 under a nitrogen atmosphere. It was slowly added dropwise for 30 minutes n-butyllithium (24.76ml, 40mmol) to the cooled solution, which was stirred for 1 hour at the same temperature. Trimethylborate (4.5g, 43mmol) was added dropwise at the same temperature was stirred overnight at room temperature. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Extraction with ethyl acetate was separated organic layer was concentrated under reduced pressure, crystallization was put in the n-hexane. To give a intermediates c-1>.

Reference： [1]Patent: KR2015/43020,2015,A .Location in patent: Paragraph 0227; 0228; 0229; 0230
[2]Patent: US2017/12214,2017,A1 .Location in patent: Paragraph 0159; 0160
[3]Patent: US10388882,2019,B2 .Location in patent: Page/Page column 62
[4]Patent: KR101515814,2015,B1 .Location in patent: Paragraph 0300; 0301
[5]Patent: KR102002025,2019,B1 .Location in patent: Paragraph 0281; 0282
[6]Patent: EP2876104,2015,A1 .Location in patent: Paragraph 0125-0126
[7]Patent: US10316013,2019,B2 .Location in patent: Page/Page column 49
[8]Patent: US2011/152587,2011,A1 .Location in patent: Page/Page column 32
[9]Patent: KR2015/128583,2015,A .Location in patent: Paragraph 0233-0238

22
[ 150-46-9 ]
[ 23674-20-6 ]
10-phenylanthracene-9-boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.2%		Exemplary Synthesis 2; Synthesis of Compound 2; Synthesis of 10-Phenylanthracene-9-Boronic Acid; An amount of 15.14 g (58.9 mmol) of 9-bromoanthracene, 7.2 g (59 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 100 ml of toluene and 25 ml of ethanol. Then, 50 ml of 2M sodium carbonate solution was added to the mixed solvent and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 13.65 g (53.7 mmol) of 9-phenylanthracene. The yield was 91.2%.An amount of 13.65 (53.7 mmol) of 9-phenylanthracene was dissolved in 100 ml of N,N dimethylformamide. An amount of 10.5 g (59 mmol) of N bromosuccinimide was added and allowed to react for six hours. Then, distilled water was added to stop the reaction and the deposit was filtered. The recovered deposit was purified by column chromatography to obtain 15.97 g (48 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>. The yield was 89.3%.An amount of 14 g (42 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in dehydrated THF and cooled to -80 C. Then, 31.2 ml (49 mmol) of a solution of n-butyllithium in n-hexane was added dropwise. Forty minutes later, 13 g (89 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was added and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 10 g (33.6 mmol) of 10-phenylanthracene-9-boronic acid. The yield was 75.2%.(Synthesis of Compound 2); An amount of 0.94 g (3.14 mmol) of 10-phenylanthracene-9-boronic acid, 1.52 g (3.14 mmol) of 9-bromo-7,12-diphenybenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.37 g (2.09 mmol) of Compound 2. The yield was 66.6%.The obtained Compound 2 was identified by the mass spectrum, infrared absorption spectrum, and NMR.

Reference： [1]Patent: US2011/295017,2011,A1 .Location in patent: Page/Page column 22
[2]Journal of Nanoscience and Nanotechnology,2016,vol. 16,p. 3102 - 3105

23
[ 23674-20-6 ]
[ 536-74-3 ]
[ 97083-12-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 80℃; for 4.5h; Sealed tube;
80%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In toluene at 110℃; for 12h; Inert atmosphere;
65%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine In tetrahydrofuran for 18h; Reflux; Inert atmosphere;

Reference： [1]Fudickar, Werner; Linker, Torsten [Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 15071 - 15082]
[2]Hong, Ju Hyun; Im, Sehee; Kim, Mingi; Kim, Na Young; Lee, Kang Mun; Ryu, Chan Hee; Seo, Yung Ju [Journal of Materials Chemistry C, 2021, vol. 9, # 31, p. 9874 - 9883]
[3]Chen, Kepeng; Gurzadyan, Gagik G.; Lei, Yanming; Tang, Geliang; Zhao, Jianzhang [Journal of Photochemistry and Photobiology A: Chemistry, 2020, vol. 398]

24
[ 23674-20-6 ]
[ 71597-85-8 ]
[ 192872-06-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; cesium fluoride; In tetrahydrofuran; water; toluene; at 120℃; for 8h;Inert atmosphere;	General procedure: In a similar manner as described previously [55]. An aqueous solution of K2CO3 (5.4 g, 39.0 mmol) and CsF (3.7 g, 24.3 mmol) was added to the solution of compound1 (5.0 g, 19.5 mmol) and phenylboronic acid (3.6 g, 25.4 mmol)in the mixed solvent of toluene (40 mL), tetrahydrofuran (60 mL) and water (10 mL). After bubbling argon through themixture for 15 min, Pd(PPh3)4 (300 mg, 0.3 mmol) was added,and the mixture was stirred and refluxed for 8 h. Then, the reaction mixture was extracted with dichloromethane, and theorganic layer was dried over anhydrous Na2SO4. The solutionwas concentrated under reduced pressure to obtain the crudeproduct which was further purified by chromatography (silicagel, dichloromethane/petroleum ether 30:1) to afford compound 2 as white solid (4.8 g, 82.0%).

Reference： [1]Chemical Communications,2013,vol. 49,p. 5639 - 5641
[2]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1601 - 1611
[3]Journal of Physical Chemistry A,2015,vol. 119,p. 468 - 481

25
[ 1257220-47-5 ]
[ 23674-20-6 ]
[ 1604713-94-1 ]

Yield	Reaction Conditions	Operation in experiment
46.5%	With potassium phosphate; copper(l) iodide; ethylenediamine; In toluene; at 120℃; for 12h;	After mixing compound A 4.5 g (0.016 mol), 9-bromo-10-phenylanthracene 6.3 g (0.019 mol), CuI 1.5 g (0.008 mol), K3PO4 10.4 g (0.049 mol), ethylenediamine (EDA) 1.1 mL (0.016 mol), and toluene 150 mL, the mixture was heated to 120C, and stirred for 12 hours. After the reaction was completed, the mixture was washed with distilled water, extracted with ethylacetate (EA), the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator, and the remaining product was separated using a column to obtain compound H-1, 4.0 g (46.5%). Melting point 307C, UV 268 nm (in methylene chloride (MC)), PL 420 nm (in MC), Molecular weight 535.68

Reference： [1]Patent: WO2014/61961,2014,A1 .Location in patent: Paragraph 125-128

26
[ 523-27-3 ]
[ 71-43-2 ]
[ 1499-10-1 ]
[ 23674-20-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 406 - 410

27
[ 23674-20-6 ]
[ 62-53-3 ]
[ 15409-87-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 100℃; for 72h;Inert atmosphere; Sealed tube;	General procedure: An oven-dried pressure tube was cooled under nitrogen and charged with 9-bromanthracene (0.5 g, 1.9 mmol), distilled aniline (0.26 mL, 2.9 mmol), NaOtBu (0.44 g, 3.8 mmol), Pd(OAc)2 (22 mg, 5 mol%) and P(tBu)3 (23 uL, 0.1 mmol). To this was added dry toluene (10 mL). The pressure tube was sealed under nitrogen and stirred at 100 C for 72 h. After 72 h, the pressure tube was cooled to rt and toluene was removed in vacuo. Subsequently, the reaction was quenched with water and the organic contents were extracted with chloroform. The combined extract was dried over anhyd Na2SO4 and filtered. The solvent was removed in vacuo and the crude product was subjected to silica gel column chromatography using CHCl3/pet.ether (5:95) as an eluent to yield pure 9-(N-phenylamino)anthracene as yellow crystalline solid (0.36 g, 70% yield)

Reference： [1]Organic electronics,2014,vol. 15,p. 3766 - 3772

28
[ 23674-20-6 ]
[ 73183-34-3 ]
[ 460347-59-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 24h; Inert atmosphere; Reflux;
63%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 95℃;	17.1 Synthesis of intermediate 17-1 9,10-dibromoanthracene (3.4 g, 0.010 mol) in bis (pinacolato) dibron (5.0 g, 0.024 mol), PdCl2 (dppf) (0.4 g, 0.0005 mol), potassium-acetate (2.7 g, 0.020 mol) into a 100 mL 1,4-dioxane and stirred for 24 hours at 95°C . The reaction was then cooled to terminate the reaction H20: After layer separation the MC column purification (n-Hexane: MC) to the intermediate 14-4 3.1 g (yield:71%) was obtained. 9-bromo-10-phenylanthracene (3.3 g, 0.010 mol) in bis (pinacolato) dibron (2.5 g, 0.012 mol) were placed in Example 14-Preparation Example 4 in the same manner as in synthesis to give the 2.4 g (63% yield).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate In toluene at 120℃; for 12h;	4; 5 Add 100mmol of M2, 100mmol of pinacol diborate, 41.4g of potassium carbonate (300mmol) and 800ml of toluene into the reaction flask, and add 1mol% of Pd2(dba)3, and react at 120°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, filtered, and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M3. Among them, the amount of Pd2(dba)3 added is 1 mol% of M2.

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃;

1 Synthesis of Intermediate 158(b) 4.2 g (12.60 mmol) of Intermediate 158(a), 4.8 g (18.91 mmol) of bis(pinacolato)diboron, 3.09 g (31.51 mmol) of potassium acetate (AcOK), and 0.46 g (0.63 mmol) of 1,1?-bis(diphenylphosphino)ferrocene] palladium(II) dichloride, Pd(dppf)Cl 2 were added to a reaction vessel, and the mixture was dissolved in 30 mL of dioxane and stirred at a temperature of 100°C. Once the reaction was complete, the resulting mixture was cooled to room temperature, and an extraction process was performed by using ethyl acetate and water to thereby obtain an organic layer. The obtained organic layer was subjected to filtration through silica gel column chromatography for concentration. The resulting solid compound Intermediate 158(b) was used in the following reaction without any further purification process. (4.1 g, yield: 86%) LC-Mass Spetrometry (calculated value: 380.19 g/mol, found value: 381.3 g/mol (M+1))

Reference： [1]He, Chuanyou; Guo, Haoqing; Peng, Qiming; Dong, Shengzhi; Li, Feng [Journal of Materials Chemistry C, 2015, vol. 3, # 38, p. 9942 - 9947]
[2]Current Patent Assignee: P&H TECH CO.,LTD. - KR2016/80420, 2016, A Location in patent: Paragraph 0353; 0383-0386
[3]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264911, 2021, A Location in patent: Paragraph 0127; 0128; 0131; 0136; 0137; 0140
[4]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD. - US2021/288259, 2021, A1 Location in patent: Paragraph 0283; 0286-0287

29
[ 23674-20-6 ]
[ 126747-14-6 ]
[ 1877285-47-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 9-bromo-10-phenylanthracene; 4-cyanophenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In toluene Stage #2: With potassium hydroxide In 2-ethoxy-ethanol; toluene

Reference： [1]Poznik; Faltermeier; Dick; König [RSC Advances, 2016, vol. 6, # 48, p. 41947 - 41950]

30
[ 1240963-55-6 ]
[ 23674-20-6 ]
[ 1165951-96-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 24h;Inert atmosphere; Reflux;	Intermediate (D) in a round bottom flask was charged 20g (60.02mmol), intermediate (I) 23.97g (66.02mmol) of toluene was added into the aqueous solution of potassium carbonate dissolved in 108ml 24.8g (180.06mmol) was dissolved was added (200ml) and It was stirred. Followed by adding thereto tetrakis triphenylphosphine palladium 1.38g (1.20mmol) was stirred and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was filtered and the dried extract was then extracted with ethyl acetate, magnesium sulfate, and the filtrate was concentrated under reduced pressure and the product n- hexane / dichloromethane (7: 3 by volume). Purification by silica gel column chromatography and, MonoChlorobenzene 400ml inCompound 6 was obtained by recrystallization as a 24.02g (70% yield).
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 24h;Inert atmosphere; Reflux;	Intermediate To a round bottom flask (D) 20g (60.02mmol), into the intermediate (I) 23.97g (66.02mmol) is toluene (200ml)And stirred was added an aqueous solution of potassium carbonate dissolved in 108ml 24.8g (180.06mmol) was dissolved in. Tet hereWas added to Mandrakis triphenylphosphine palladium 1.38g (1.20mmol) was stirred and refluxed for 24 hours under a nitrogen atmosphere. halfAfter drying and filtration the end Huh extract after extraction with ethyl acetate, magnesium sulfate, and was concentrated under reduced pressure and the filtrateAll. The product n- hexane / dichloromethane: obtain (7: 3 by volume) as a silica gel column chromatography and Compound 1-77 was recrystallized with monochlorobenzene to give a 400ml 24.02g (70% yield).

Reference： [1]Patent: KR2016/12846,2016,A .Location in patent: Paragraph 0206; 0207; 0210; 0211
[2]Patent: KR2016/22081,2016,A .Location in patent: Paragraph 0454; 0455; 0458; 0459

31
[ 950779-13-2 ]
[ 23674-20-6 ]
1,6-bis(10-phenylanthracene-9-yl)pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 110℃; for 48h; Inert atmosphere;	1.2 Under a nitrogen atmosphere 250ml flask, two shoe ranks 1,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene 4.00g (8.8mmol) to be added 9-bromo-10- phenylanthracene 6.43g (19.3mmol), palladium tetrakis (triphenylphosphine) 0.41g (0.4mmol) as a catalyst. Then insert a potassium carbonate aqueous solution and 60mL of 2M 100ml toluene was allowed to react for 48 hours at 110 . After the reaction, extract the organic layer with distilled water, and the chloroform was dried with magnesium sulfate chamberAfter removal of the catalyst by chromatography using silica gel and recrystallization from toluene, through the sublimation purification1,6-bis (10-phenyl anthracene-9-yl) pyrene was obtained as a 4.07g (66%) yield.

Reference： [1]Current Patent Assignee: KOREA NATIONAL UNIVERSITY OF TRANSPORTATION INDUSTRY - KR2015/103510, 2015, A Location in patent: Paragraph 0160-0162

32
[ 23674-20-6 ]
C₁₇H₁₂BNO₃ [ No CAS ]
C₃₇H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 120℃; for 8h;Inert atmosphere;	Under nitrogen compound A-4 (10.38 g, 35.90 mmol), compound A-5 (10.88g, 32.64 mmol) in tetrahydrofuran(THF) was dissolved in 200ml. Water 100 mL dissolved in potassium carbonate(14.89 g, 107.7 mmol), tetrakis (triphenyl-phosphine) palladium (tetrakis(triphenyl-phosphine) palladium) (1.25 g, 1.08 mmol) and the mixture 120 C byheating to 8 while the reaction time was reflux. After the completion of thereaction remove the water layer, the organic layer dichloromethane(dichloromethane; DCM) and extracted with. Water was removed with anhydrousMgSO4, filter and was concentrated under reduced pressure. Recrystallizationwas concentrated to CHCl3 / EtOH to obtain a compound of formula 2-6 (15.36 g,30.87 mmol, 91%).

Reference： [1]Patent: KR2015/136033,2015,A .Location in patent: Paragraph 0325; 0331; 0336; 0337

33
[ 121-43-7 ]
[ 23674-20-6 ]
[ 7732-18-5 ]
10-phenylanthracene-9-boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.3%		<1-c> was synthesized by the following Scheme 3. In a 5000 mL round bottom flask, 360.21 g (1.085 mol) of <1-b> obtained from Scheme 2 were dissolved in 2900 mL of tetrahydrofuran under a nitrogen atmosphere and cooled to minus 70 degrees. After cooling, 813.68 mL (1.302 mol) of n-butyllithium (1.6 M hexane solution) is slowly added dropwise. After completion of the dropwise addition, the mixture was stirred for 2 hours and then trimethylborate 181.44 mL (1.627 mol) was added dropwise and stirred at room temperature for 12 hours.After completion of the reaction, 900 mL of 2 N hydrochloric acid solution was added thereto, stirred for 30 minutes, and ethyl acetate and water were added for extraction. The organic layer is anhydrous and concentrated under reduced pressure. When the solid precipitates during concentration under reduced pressure, add hexane, stir for 30 minutes, and filter 305.0 g (yield 94.3%) of <1-c> were obtained.
76.7%		<strong>[23674-20-6]9-phenyl-10-bromo-anthracene</strong> (13.4 g, 40 mmol) was dissolved in 110 mL THF. In the cooling state up to -78C was put in the n-BuLi (30 mL) slowly. At the end of the addition and then stirred for about 1 hour at -78C was put trimethyl borate (5.9 g, 56 mmol). After 1 hour stirring at -78C stirred at room temperature for about two hours and put in a 2 N HCl was adjusted to acidic. The solvent was then extracted with EA and obtained with hexane to give the 9-phenyl-10-anthracene boronic acid 9.2g (yield 76.7%).
76.7%		9-phenyl-10-bromoanthracene (13.4 g, 40 mmol) was dissolved in 110 mL of THF. The n-BuLi (30 mL) was added slowly while cooling to -78 C. After the addition, trimethylborate (5.9 g, 56 mmol) was added at -78 C for about 1 hour. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for 2 hours and 2N HCl was added to adjust the acidity. EA followed by removal of the solvent to obtain 9.2 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).

76.7%		In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity.After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7%		In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C. After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity. After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7%		In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity.After extraction with EA and removal of the solvent, crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7%		9-phenyl-10-bromoanthracene(13.4 g, 40 mmol) was dissolved in 110 mL of THF. Cooled to -78 n-BuLi (30 mL) was added slowly. After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (5.9 g, 56 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust the acidity.After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 9-phenyl-10-anthraceneboronic acid.9.2g (yield 76.7%) was obtained.

Reference： [1]Patent: KR102013399,2019,B1 .Location in patent: Paragraph 0169; 0183-0188
[2]Patent: KR101503766,2015,B1 .Location in patent: Paragraph 0206; 0212; 0218-0219
[3]Patent: KR101920345,2018,B1 .Location in patent: Paragraph 0283; 0289; 0290
[4]Patent: KR101554591,2015,B1 .Location in patent: Paragraph 0255; 0262; 0263; 0343; 0350; 0351
[5]Patent: KR101521101,2015,B1 .Location in patent: Paragraph 0238; 0245; 0246
[6]Patent: KR102051952,2019,B1 .Location in patent: Paragraph 0285-0286; 0292-0293
[7]Patent: KR102066709,2020,B1 .Location in patent: Paragraph 0206; 0258; 0264; 0265

34
[ 93-58-3 ]
[ 123335-02-4 ]
[ 602-55-1 ]
[ 23674-20-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 52% 2: 19%	Stage #1: bis-(2-bromophenyl)methanol With isopropylmagnesium chloride; magnesium In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: benzoic acid methyl ester In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #3: With hydrogen bromide In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Link, Achim; Fischer, Christian; Sparr, Christof [Synthesis, 2017, vol. 49, # 2, p. 397 - 402]

35
[ 93-58-3 ]
[ 123335-02-4 ]
[ 23674-20-6 ]

Yield	Reaction Conditions	Operation in experiment
65%		A solution of 9 (prepared as described from 200 mumol methyl benzoate) at 0 C was cannulated (and by this separated from residual Mg) into a solution of BF3·OEt2 (103 muL, 400 mumol) in glacial AcOH (500 muL). The mixture was vigorously stirred at 60 C for 1 h. H2O (5.0 mL) and Et2O (10 mL) were added. The phases were separated and the aqueous phase was extracted with Et2O (2 × 10 mL). The combined organic phases were washed with brine (10 mL) and dried over Na2SO4. The solvent was removed in vacuo and the crude was purified by chromatography (pentane) to give a slightly yellow solid.

Reference： [1]Synthesis,2017,vol. 49,p. 397 - 402

36
[ 23674-20-6 ]
[ 86-74-8 ]
9-(10-phenylanthracene-9-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.3%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In N,N-dimethyl-formamide; at 153℃;Inert atmosphere;	0.3120 mol of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>, 0.2400 mol of carbazole, 0.0184 mol of phenanthroline, cuprous iodide0.0184 mol, cesium carbonate 0.4080 mol was charged into a 1000 ml three-necked flask, dissolved in 300 ml of DMF, evacuated to nitrogenThree times, the temperature to 153 C, the reaction overnight. The reaction solution was passed through a silica gel funnel and rinsed with methylene chloride until no product was releasedAbout 400ml with 500ml of water, liquid, take dichloromethane phase, washed with water three times; spin dry, add 100ml dissolved, add500ml ethanol has a large amount of solid precipitation, suction filtration, vacuum drying at 55 . The product was 0.2119 mol, yield 88.30%.

Reference： [1]Patent: CN104650043,2017,B .Location in patent: Paragraph 0055; 0056; 0057; 0058

37
[ 23674-20-6 ]
[ 905947-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 4 h / -78 °C 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water; ethanol / 5 h 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 12 h / -78 °C

Reference： [1]Current Patent Assignee: TDK CORPORATION - JP2016/183140, 2016, A

38
[ 23674-20-6 ]
[ 1023674-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 4 h / -78 °C 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water; ethanol / 5 h
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1.33 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 - 20 °C / Inert atmosphere 1.3: 0.5 h / Inert atmosphere; Cooling with ice 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol; water / 16 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -70 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 1.3: 0.5 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 12 h / Reflux

Reference： [1]Current Patent Assignee: TDK CORPORATION - JP2016/183140, 2016, A
[2]Current Patent Assignee: TDK CORPORATION - JP2016/150920, 2016, A
[3]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR102013399, 2019, B1

39
[ 23674-20-6 ]
[ 145238-17-1 ]
C₅₂H₃₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 24h; Inert atmosphere; Reflux;	1 Synthesis of Compound 1 Compound A 8.0 g (31.27 mmol),Compound 1 21.88 g (65.67 mmol),10.37 g (75.05 mmol) of K2CO3 and 1.08 g (0.94 mmmol) of Pd (PPh3) 4 were placed in 150 mL of toluene / 80 mL of distilled water (DIW) and refluxed under nitrogen stream for 24 hours. The resulting solid was filtered, and the obtained solid was dissolved in chlorobenzene, and the organic layer was subjected to silica gel filtration. The organic solution was then removed and washed with chlorobenzeneAnd recrystallized to obtain 16.83 g (yield: 80%) of Compound 1.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydroxide In water Inert atmosphere; Reflux;	2 Example 2: Preparation of L5 After adding a certain amount of D5 and K5 to the three-necked bottle, install a mechanical stir bar.Nitrogen gas was introduced for 20 minutes, and the catalyst was added under the protection of nitrogen.Pd (PPh3) 40.25-3 mol%, 2M alkali solution 0.018 mol, heated to reflux,Reaction for 5-10 hours,After the reaction, it was suction filtered, washed with toluene and washed with ethanol. After recrystallization from xylene, the purity is 99%.The above powder. To further increase the purity of L5,Sublimation by one or more times using a vacuum sublimation instrument,Can get more than purity99.5% of L5 products.

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - KR2017/96860, 2017, A Location in patent: Paragraph 0123-0126
[2]Current Patent Assignee: AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN109867646, 2019, A Location in patent: Paragraph 0127-0132

40
[ 23674-20-6 ]
[ 13922-41-3 ]
[ 63018-93-9 ]

Yield	Reaction Conditions	Operation in experiment
65.8%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene for 2h; Inert atmosphere; Reflux;	1.e (e) Synthesis of compound-5 The reaction solution of the upper part was added to naphthaleneboronic acid (17.2 g, 100 mmol) and tetraphenylphenylphosphine palladium (5.78G, 5 mmol) was refluxed under nitrogen for 2 hours, cooled to room temperature, a large amount of solid was precipitated, the solid was filtered,Washed with water (100 ml x 3), dried, toluene (100 ml x 3) hot and dried to give 25 g of a white solidHPLC = 97.2%, yield = 65.8%.

Reference： [1]Current Patent Assignee: EVERDISPLAY OPTRONICS (SHANGHAI) LIMITED - CN107216347, 2017, A Location in patent: Paragraph 0046; 0047; 0057; 0058

41
[ 23674-20-6 ]
[ 1421789-05-0 ]
[ 2194590-43-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	16 PREPARATION EXAMPLE 16 Preparation of Compound 1-1 Compound F (5.0 g, 15.0 mmol)And Compound K (5.9 g, 16.5 mmol), Pd (t-Bu3P) 2 (0.01 g, 0.02 mmol) was added to a 2 M aqueous K 2 CO 3 solution (20 mL) and THF (200 mL), and the mixture was refluxed and stirred for about 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized from toluene / EtOAc to obtain Compound 1-1 (7.0 g, 82%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2018/20108, 2018, A Location in patent: Paragraph 0250; 0251

42
[ 23674-20-6 ]
[ 1224976-40-2 ]
[ 2185862-32-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	21 PREPARATION EXAMPLE 21 Preparation of Compound 2-1 Compound F (5.2 g, 15.7 mmol)And compound L (5.0 g, 14.3 mmol),Pd (t-Bu3P) 2 (0.01 g, 0.02 mmol) was added to a 2 M aqueous K 2 CO 3 solution (20 mL) and THF (200 mL), and the mixture was refluxed and stirred for about 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized from toluene / EtOAc to obtain Compound 2-1 (6.2 g, 76%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2018/20108, 2018, A Location in patent: Paragraph 0275; 0276

43
[ 23674-20-6 ]
C₃₀H₂₅BO₄ [ No CAS ]
C₄₄H₂₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With palladium diacetate; potassium carbonate; CyJohnPhos; In ethanol; water; toluene; at 80℃; for 16h;Inert atmosphere;	In Synthetic Mechanism I, Intermediate A (1.05 eq), Reactant An (1.0 eq), Pd(OAc) 2 (0.01 eq), PCy2 (2-biPh) (0.04 eq)Mix with potassium carbonate (2.0 eq) in toluene (30 ml),a mixed solution of ethanol (3 ml) and water (3 ml), thenThe mixed solution was heated to reflux under a nitrogen atmosphere and stirring was continued for 16 hours.After the reaction is completed and the temperature is lowered to room temperature, extraction is carried out in the organic layer to collect the crude product.After drying over magnesium sulfate, filtration and separation and drying,After purification by silica gel column chromatography, 12.0 g of a white solid product was obtained.That is, the novel compound of the present invention.The intermediates A and reactants An used in the synthesis of compounds 1 to 22 are listed in Table 8 below.

Reference： [1]Patent: CN108623546,2018,A .Location in patent: Paragraph 0258; 0259

44
(4-benzoylphenyl)boronic acid [ No CAS ]
[ 23674-20-6 ]
C₃₃H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 72h;	<strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> (0.20 g, 0.60 mmol), 4-benzoylphenylboronic acid (0.28 g, 1.26 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.18 mmol) were mixed with 50 mL of tetrahydrofuran (THF) at room temperature, and 25 mL of 2N K2CO3 (aq) was added thereto. The mixed solution was heated at a temperature of 70 C. for 72 hours. Water and CH2Cl2 were added to the reaction mixture obtained therefrom and shaken violently to extact a reaction product dissolved in a CH2Cl2 layer. Then, MgSO4 was added thereto so as to remove water dissolved in the CH2Cl2 layer, and filtering was performed thereon by using a glass filter. The resulting product obtained therefrom was purified by silica gel column chromatography using CH2Cl2:n-hexane (1:2 (v/v)) to obtain Compound 2 (yellow powder, yield of 96%). 1H NMR (300 MHz, CDCl3) delta (ppm): 7.33-7.40 (m, 4H), 7.47-7.50 (m, 2H), 7.55-7.66 (m, 8H), 7.67-7.74 (m, 4H), 7.97-8.00 (m, 2H), 8.08 (d, J=1.8 Hz, 2H). 13C NMR (126 MHz, CD2Cl2) delta (ppm): 30.36, 125.68, 125.92, 127.07, 127.57, 128.15, 128.94, 129.02, 130.14, 130.40, 130.61, 130.72, 131.78, 131.95, 133.05, 136.38, 137.41, 138.28, 139.39, 144.24, 196.75.

Reference： [1]Patent: US2019/74445,2019,A1 .Location in patent: Paragraph 0223-0226

45
[ 1260865-91-5 ]
[ 23674-20-6 ]
C₄₆H₃₂ [ No CAS ]

Reference： [1]ChemPlusChem,2019,vol. 84,p. 746 - 753

46
[ 23674-20-6 ]
[ 1447669-03-5 ]
C₆₆H₄₄ [ No CAS ]

Reference： [1]ChemPlusChem,2019,vol. 84,p. 746 - 753

47
[ 196491-93-7 ]
[ 23674-20-6 ]
[ 2397744-96-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 9-bromo-10-phenylanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine In tetrahydrofuran; hexane at -78 - 20℃; for 9.5h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water for 4h; Inert atmosphere; Reflux;	2.2 2)9-bromo-10-phenylindole(16.66g, 50mmol)Solubilized in 100ml tetrahydrofuran500ml three-necked bottle,Cool down to -78 ° C,Slowly add 1.6M (22g, 52mmol) under nitrogen protectiona solution of n-butyllithium in n-hexane, reacted at -78 ° C for 2 h,Add under nitrogen protection2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine (9.45 g, 25 mmol)Continue to react for 1.5 h, then return to room temperature for 8 h.Add 50 ml of tin dichloride (9.86 g, 52 mmol) under nitrogen.The mass fraction is 10% hydrochloric acid heated to reflux for 4 h,The TLC monitoring reaction was completed. After cooling to room temperature, filter,After distilling off the solvent under reduced pressure, the solid was washed with acetone (200 ml), toluene was recrystallized twice and dried under vacuum to give intermediate(4R,8S)-2,6-dibromo-4,8-bis(10-benzofluoren-9-yl)benzo[1,2-b:4,5-b']dithiophene16.20g,The yield was 76%.

Reference： [1]Current Patent Assignee: WUHAN SHANGSAI OPTOELECTRONICS TECHNOLOGY CO LTD - CN109851625, 2019, A Location in patent: Paragraph 0071; 0074

48
[ 23674-20-6 ]
C₃₄H₂₇BO₃ [ No CAS ]
C₄₈H₂₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.3%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere;	General procedure: 2 g (3.8 mmol) of intermediate A3,1.1 g (7.6 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine,0.08 g (0.07 mmol) of tetrakis (triphenylphosphine) palladium, 4 ml of 2M sodium carbonate (aqueous solution), 10 ml of ethanol,With 30 ml of toluene, the mixture was degassed and placed under nitrogen, and then heated at 100 C for 12 hours.After the reaction was completed, the mixture was cooled to room temperature.Subsequently, the organic layer was extracted with dichloromethane and water, and then dried over anhydrous magnesium sulfate. After removing the solvent, the residue was purified by silica column chromatography to obtain compound C41 (2.2 g, 53%).
76.3%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 100℃; for 12h;Inert atmosphere;	General procedure: A mixture of 2 g (3.8 mmol) of Intermediate A3, 1.1 g (7.6 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.08 g (0.07 mmol) of Pd(PPh3)4, 4 ml of 2M Na2CO3(aq), 10 ml of EtOH, and 30 ml of toluene was degassed and placed under nitrogen, and then heated at 100 C. for 12 hrs. After the reaction finished, the mixture was allowed to cool to room temperature. Subsequently, the organic layer was extracted with dichloromethane and water, and then dried with anhydrous MgSO4. After the solvent was removed, the residue was purified by column chromatography on silica to give compound C41 (2.2 g, 53%). MS(m/z, EI+): 1117.25.

Reference： [1]Patent: CN111004168,2020,A .Location in patent: Paragraph 0078; 0090-0092; 0110-0113
[2]Patent: US2020/109138,2020,A1 .Location in patent: Paragraph 0023; 0031-0032; 0045-0047

49
[ 23674-20-6 ]
[ 1877285-47-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane 2: lithium hydroxide / methanol

Reference： [1]He, Zhifeng; Hu, Qingang; Pu, Yumei; Wang, Jianquan; Wang, Yuxin; Xia, Chengwan; Xiao, Qi; Yin, Honglin; Zhang, Qian [RSC Advances, 2020, vol. 10, # 47, p. 28314 - 28323]

50
[ 372521-91-0 ]
[ 23674-20-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	1 Manufacturing example 1-8 Combine 9-bromo-10-phenylanthracene (A, 10g, 30.1mmol) with (4-phenylnaphthalene-1-yl)boronic acid ((4-phenylnaphthalene-1-yl) Boronic acid) (B, 9g, 36.1mmol), Pd(t-Bu3P)2 (0.8g, 0.15mmol) were dissolved in 2M K2CO3 aqueous solution (30mL) and THF (100mL), and stirred under reflux for about 12 hours. After the reaction, it was cooled to room temperature, the organic layer was separated in the reaction mixture, the organic layer was dried with magnesium sulfate, and after distillation under reduced pressure, it was recrystallized with Tol (toluene)/EA (ethyl acetate) to produce Production Example 1 -8 compound (12.8 g, 93%).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - CN108463535, 2021, B Location in patent: Paragraph 0175-0179

51
[ 23674-20-6 ]
[ 145238-17-1 ]
C₃₂H₂₁BO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.2 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;	10 Synthesis Example 10 Synthesis of Compound 85 500 ml three-neck flask, nitrogen protection, add 100 ml toluene, 30 ml ethanol, 30 ml water, then add 2.56 g (0.01 mol) dibenzo[b,d]furan-4,6-diboronic acid, 3.33 g (0.01 mol) dibenzo[b,d]furan-4,6-diboronic acid mol) 9-bromo-10 phenylanthracene, 2.12 grams (0.02mol) of sodium carbonate, 0.115 grams (0.0001mol) of tetrakistriphenylphosphine palladium, slowly warming up to reflux reaction for 8 hours, cooling, adding water, the organic layer was washed with water Then, add magnesium sulfate and a small amount of 200-300 mesh silica gel to dry, filter to remove magnesium sulfate and silica gel, remove the solvent under reduced pressure, separate by silica gel column chromatography, first wash with petroleum ether:ethyl acetate=10:1 (volume ratio) Then, gradually increase the polarity of the elution solvent to petroleum ether:ethyl acetate=3:1 (volume ratio) to obtain 2.2 g of the compound represented by M-85-1.

Reference： [1]Current Patent Assignee: BEIJING SINEVA TECHNOLOGY CO LTD - CN114057681, 2022, A Location in patent: Paragraph 0080-0082

52
[ 23674-20-6 ]
[ 947770-80-1 ]
[ 1416962-85-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate In toluene at 90℃;	3 3. Synthesis of Compound 2-3 The compound I2-3a (2.0 g, 6.0 mmol), the compound I2-3b (1.9 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-3 (2.0 g) as a white powder. (yield 79%)
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate In toluene at 90℃;	3 3. Synthesis of Compound 2-3 The compound I2-3a (2.0 g, 6.0 mmol), the compound I2-3b (1.9 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-3 (2.0 g) as a white powder. (yield 79%)
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate In toluene at 90℃;	3 3. Synthesis of Compound 2-3 The compound I2-3a (2.0 g, 6.0 mmol), the compound I2-3b (1.9 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-3 (2.0 g) as a white powder. (yield 79%)

79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate In toluene at 90℃;	3 3. Synthesis of Compound 2-3 The compound I2-3a (2.0 g, 6.0 mmol), the compound I2-3b (1.9 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added into the mixture. The reactant was stirred and heated at 90′° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-3 (2.0 g) as a white powder. (yield 79%)
79%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate In toluene at 90℃;	11 Synthesis Example 11: Synthesis of Compound 2-3 Compound 2-3A (2.0 g, 6.0 mmol), Compound 2-3B (1.9 g, 6.6 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol) and toluene (50 ml) were put into a 250 ml reaction vessel in a dry box. The reaction vessel was removed from the dry box, and then sodium carbonate anhydrous (2M, 20 ml) was added into the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, an organic layer was separated. An aqueous layer was washed with dichloromethane and the organic layer was concentrated with rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified with silica-gel column chromatography to give Compound 2-3 (2.0 g, yield: 79%) of white powder.
89 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;	2 Comparative example 2: Accurately weigh the compound 9-bromo-10-phenylanthracene (15g, 45mmol), dibenzofuran-2-boronate (13.2g, 45mmol), tetrakistriphenylphosphine palladium (2.5g, 2.2mmol), Potassium carbonate (12.4g, 90mmol) was sequentially added to a 500mL three-neck flask, 1500mL of dioxane and 30mL of water were added, the temperature was raised to 90°C for overnight reaction after pumping and filling with nitrogen three times.After the reaction, cool the reaction solution to room temperature, add 300mL of water, then extract with DCM (300mL*3), combine the organic phases and dry with anhydrous sodium sulfate, distill off excess solvent under reduced pressure, and use toluene and n-hexane volume ratio 10:3 for recrystallization, the target product 16.8g was obtained, and the yield was about 89%.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216407, 2022, A1 Location in patent: Paragraph 0149; 0150
[2]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216409, 2022, A1 Location in patent: Paragraph 0137; 0138
[3]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216408, 2022, A1 Location in patent: Paragraph 0139-0140
[4]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/209120, 2022, A1 Location in patent: Paragraph 0137-0138
[5]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216410, 2022, A1 Location in patent: Paragraph 0241-0242
[6]Current Patent Assignee: ZHEJIANG BRILLIANT OPTOELECTRONIC TECH - WO2022/247858, 2022, A1 Location in patent: Page/Page column 28

53
[ 23674-20-6 ]
[ 2609690-07-3 ]
[ 2033132-20-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; anhydrous sodium carbonate In toluene at 90℃;	4 4. Synthesis of Compound 2-4 The compound I2-4a (2.0 g, 6.0 mmol), the compound I2-4b (2.4 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-4 (2.0 g) as a white powder. (yield 67%)
67%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; anhydrous sodium carbonate In toluene at 90℃;	4 4. Synthesis of Compound 2-4 The compound I2-4a (2.0 g, 6.0 mmol), the compound I2-4b (2.4 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-4 (2.0 g) as a white powder. (yield 67%)
67%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; anhydrous sodium carbonate In toluene at 90℃;	4 4. Synthesis of Compound 2-4 The compound I2-4a (2.0 g, 6.0 mmol), the compound I2-4b (2.4 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added int the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-4 (2.0 g) as a white powder. (yield 67%)

67%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; anhydrous sodium carbonate In toluene at 90℃;	4 4. Synthesis of Compound 2-4 The compound I2-4a (2.0 g, 6.0 mmol), the compound I2-4b (2.4 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), and toluene (50 mL) were added into a 250 mL reactor in a dry box. After the reactor is removed from the dry box, and sodium carbonate anhydrous (2M, 20 mL) was added into the mixture. The reactant was stirred and heated at 90° C. overnight. The reaction was monitored by high-performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was subjected to purification using alumina, precipitation using hexane, and column chromatography using silica gel to obtain the compound 2-4 (2.0 g) as a white powder. (yield 67%)
67%	With tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium; anhydrous sodium carbonate In toluene at 90℃;	12 Synthesis Example 12: Synthesis of Compound 2-4 Compound 2-4A (2.0 g, 6.0 mmol), Compound 2-4B (2.4 g, 6.6 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol) and toluene (50 ml) were put into a 250 ml reaction vessel in a dry box. The reaction vessel was removed from the dry box, and then sodium carbonate anhydrous (2M, 20 ml) was added into the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, an organic layer was separated. An aqueous layer was washed with dichloromethane and the organic layer was concentrated with rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified with silica-gel column chromatography to give Compound 2-4 (2.0 g, yield: 67%) of white powder.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216407, 2022, A1 Location in patent: Paragraph 0151; 0152
[2]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216409, 2022, A1 Location in patent: Paragraph 0139; 0140
[3]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216408, 2022, A1 Location in patent: Paragraph 0139-0140
[4]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/209120, 2022, A1 Location in patent: Paragraph 0139-0140
[5]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2022/216410, 2022, A1 Location in patent: Paragraph 0243-0244

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	23674-20-6	MDL No. :	MFCD00230983
Formula :	C₂₀H₁₃Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHGGVVHVBFMGSG-UHFFFAOYSA-N
M.W :	333.22	Pubchem ID :	4155836
Synonyms :

Num. heavy atoms :	21
Num. arom. heavy atoms :	20
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	94.59
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.58 cm/s

Log Po/w (iLOGP) :	3.44
Log Po/w (XLOGP3) :	6.7
Log Po/w (WLOGP) :	6.42
Log Po/w (MLOGP) :	6.08
Log Po/w (SILICOS-IT) :	6.26
Consensus Log Po/w :	5.78

[ CAS No. 23674-20-6 ] {[proInfo.proName]}

Quality Control of [ 23674-20-6 ]

Related Doc. of [ 23674-20-6 ]

Product Details of [ 23674-20-6 ]

Calculated chemistry of [ 23674-20-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 23674-20-6 ]

Application In Synthesis of [ 23674-20-6 ]

[ 23674-20-6 ] Synthesis Path-Upstream 1~1

[ 23674-20-6 ] Synthesis Path-Downstream 1~53

Related Functional Groups of
[ 23674-20-6 ]

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-6.77
Solubility :	0.0000571 mg/ml ; 0.000000172 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.5
Solubility :	0.000104 mg/ml ; 0.000000313 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.09
Solubility :	0.000000272 mg/ml ; 0.0000000008 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P321
P322
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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling