[ CAS No. 1246308-80-4 ] {[proInfo.proName]}

Name: 1246308-80-4|4-(2-Nitrophenyl)dibenzo[b,d]furan|97%
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Quality Control of [ 1246308-80-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1246308-80-4 ]

CAS No. :	1246308-80-4	MDL No. :	MFCD28964845
Formula :	C₁₈H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZPVONLLRBPTGCG-UHFFFAOYSA-N
M.W :	289.28	Pubchem ID :	66797872
Synonyms :

Safety of [ 1246308-80-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1246308-80-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1246308-80-4 ]

[ 1246308-80-4 ] Synthesis Path-Downstream 1~3

1
[ 100124-06-9 ]
[ 577-19-5 ]
[ 1246308-80-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene for 12h; Reflux;	Reaction Formula 10a Bromonitrobenzene 20 g (99 mmol), dibenzothran1-yl-boronic acid (25.1 g, 118.8 mmol), Pd(pph3)4 (4.583.96 mmol) and Na2CO3 (31.5 g, 297 mmol) were dissolved in a mixture of ethyl alcohol (148 mE) and toluene (267 mE). The mixture was refluxed/stirred for 12 hours. After completion of the reaction, the resultant was extracted by distilled water and colunmed in a silica-gel such that 4-(2- nitrophenyl)dibenzo[b,d]furan (29.3 g, yield: 100%) was obtained.
99.7%	With potassium carbonate In ethanol; water; toluene for 24h; Reflux;	1 After dissolving dibenzo[b,d]furan-4-yl boronic acid (30 g, 142 mmol), 1-bromo-2-nitrobenzene (23.8 g, 118 mmol), K2CO3 (39.1 g, 283 mmol) and Pd(PPh3)4 (6.8 g, 5.8 mmol) in a mixture of toluene (600 mL), EtOH (150 mL) and purified water (150 mL), the reaction mixture was stirred under reflux for 24 hours. After terminating the reaction, the reaction mixture was cooled to room temperature, and an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with MC, and was filtered to obtain compound 1-2 (34 g, 99.7 %).
98%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 3h; Reflux;	9 Preparation of compound 9-1 After putting dibenzo[b,d]furan-4-ylboronic acid (20 g, 94.3 mmol), 2-bromonitrobenzene (17 g, 84.9 mmol), Pd(PPh3)4 (4.9 g, 4.24 mmol), K2CO3(23.5 g, 169.8 mmol), toluene (100 mL), EtOH (50 mL), and purified water (50 mL), the reaction mixture was stirred for 3 hours under reflux. After terminating the reaction, the reaction mixture was cooled to room temperature, the aqueous layer was removed, and the organic layer was dried with MgSO4, was filtered, was distillated under reduced pressure to remove the solvent, and was filtered through silica gel. The remaining solution was concentrated under reduced pressure to obtain compound 9-1 (24 g, 98 %).

98%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;
96%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 16h; Inert atmosphere; Reflux;	1.2 2 Preparation of (4-(2-nitrophenyl)dibenzo[b,d]furan): 6 g of dibenzofuran-4-boronic acid (1.1 eq) and o-bromonitrobenzene (1 eq), potassium carbonate (2 eq), dissolved in tetrahydrofuran: water = 3:1 (volume ratio), N2 was extracted three times.To ensure the oxygen-free environment of the system, the catalyst tetrakistriphenylphosphine palladium (2.5% eq) was added under the protection of N2, and the reaction was carried out under reflux for 16 h.After the completion of the reaction, the tetrahydrofuran was distilled off under reduced pressure, dissolved in dichloromethane, and the organic phase was washed with water, and the aqueous phase was extracted three times, and the mixture was mixed with petroleum ether.The methylene chloride mixed solvent was passed through the column to obtain a bright yellow gel (96%);
96%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 16h; Inert atmosphere; Reflux;	4.2 (2) In a 500 ml three-necked flask, 6 g of 4-benzoic acid dibenzofuran (28 mmol, 1.1 eq) and 5.05 g of o-bromonitrobenzene (25 mmol), 6.9 g of potassium carbonate (50 mmol, 2 eq) were dissolved in tetrahydrofuran: Water = 3:1 (volume ratio) a total of 200ml, pumping N2 three times to ensure the system's oxygen-free environment, under the protection of N2, the catalyst tetrakis(phenyltriphenylphosphine) palladium 0.72g (0.62mmol,2.5% eq), the reaction is carried out under reflux for 16 h. After the reaction is completed, the tetrahydrofuran is distilled off under reduced pressure, dissolved in dichloromethane, the organic phase is washed with water, the aqueous phase is extracted three times, and the mixture is mixed with petroleum ether and dichloromethane. Pass the column and get a bright yellow gel4-(2-nitrophenyl)dibenzo[b,d]furan7.0 g (yield 96%).
93%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	13 4-dibenzofuran boronic acid 20g (94.3mmol) in a round bottom flask, 2-bromo-nitro-benzene into 19.05g (94.3mmol) toluicAdding a yen (313ml) solution of potassium carbonate dissolved in 117ml 19.5g (141.5mmol) was dissolved was added and stirredIt was. Followed by adding thereto tetrakis triphenylphosphine palladium 1.09g (0.94mmol) after the ring for 12 hours under a nitrogen atmosphereRyu was stirred. After the reaction was filtered and the dried extract was then extracted with ethyl acetate, magnesium sulfate, filtered,The solution was concentrated under reduced pressure. To: (1 volume ratio 9) by column chromatography on silica gel, the product n- hexane / ethyl acetateTo give the desired compound of intermediate M-35 to give the 25.4g (93% yield).
93%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	1 Synthesis Example 1: Synthesis of Intermediate M-1 20 g (94.3 mmol) of 4-dibenzofuranboronic acid and 19.05 g (94.3 mmol) of 2-bromonitro-benzene were put in a round-bottomed flask, 313 ml of toluene was added thereto to dissolve them, and 117 ml of an aqueous solution prepared by dissolving 19.5 g (141.5 mmol) of potassium carbonate was added thereto and then, stirred. Subsequently, 1.09 g (0.94 mmol) of tetrakistriphenyl phosphine palladium was added thereto and then, refluxed and stirred under a nitrogen atmosphere for 12 hours. When a reaction was complete, an extraction solution obtained by performing extraction with ethylacetate was dried with magnesium sulfate and filtered, and a filtrate therefrom was concentrated under a reduced pressure. A product therefrom was purified through silica gel column chromatography with n-hexane/dichloromethane (a volume ratio of 7:3) to obtain 25.4 g of Intermediate M-1 as a target compound (a yield=93%). (0127) LC-Mass (theoretical value: 289.07 g/mol, measured value: M+1=290.16 g/mol)
92%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 12h; Inert atmosphere; Reflux;	8 Synthesis of Compound 8-1 Dibenzofuran-4-boronic acid (10.6 g, 50 mmol) and o-bromonitrobenzene (10.3 g, 50 mmol) were placed in a three-necked flask, stirred and dissolved with 200 mL of toluene, nitrogen-protected, and then Pd (PPh3) was added. 4 (2.83 g, 2.5 mmol) and an aqueous solution of potassium carbonate (13.8 g, 0.1 mol). The reaction mixture was stirred and refluxed for 12 hours.The organic phase was separated by cooling and washed three times with 100 mL of water.The solvent was evaporated and the residue was stirred with DCM /EtOAc.Filtration with a yellow solid gave Compound 8-1 (14.31 g, yield: 92%).
87%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 24h; Reflux;	4 Preparation of compound 95-3 [185] After dissolving compound 95-1 (127 g, 0.60 mmol), compound 95-2 (100 g, 0.50 mmol), K2CO3 (159 g, 1.50 mmol), and Pd(PPh3)4 (29 g, 0.03 mmol) in a mixture solvent of toluene (3 L), EtOH (750 mL), and purified water (750 mL), the mixture was stirred for 1 day under reflux. The obtained organic layer was extracted with ethylacetate (2 L) and washed with distilled water (500 mL). The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The crude product was purified through silica gel column chromatography and recrystallization to obtain compound 95-3 (126 g, 87 %).
87%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 24h; Reflux;	1 Example 1; Preparation of compound C-98; Preparation of compound C-98-3 After adding 4-dibenzofuranboronic acid (compound C-98-1) 127g (0.60mol), 2-bromo-nitrobenzene lOOg (0.50mol), potassium carbonate 159g (1.50mol), and tetrakis (triphenylphosphine)palladium [Pd(PPh3)4] 29g (0.03mol) in toluene 3L, ethanol 750mL and purified water 750mL, the mixture was stirred under reflux for a day. The mixture was extracted with ethyl acetate 2L. The obtained organic layer was washed with distilled water 500 mL, dried with anhydrous magnesium sulfate, and the organic solvent was then removed under reduced pressure. The obtained solid was separated by silica gel column chromatography and recrystallization to obtain compound C-98-3 (126g, 87%).
85%	With potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	5 1-bromo-2-nitrobenzene (39g, 0.19mol), dibenzo[b,d]furan-4-ylboronic acid (45g, 0.21mol), Pd(PPh3)4 (11.1g, 0.0096mol), 2M K2CO3 aqueous solution 290mL, EtOH 290mL and toluene 580mL were mixed and then heated to 120°C with stirring for 4 hours. After termination of the reaction, the mixture was washed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 5-1 (47g, 85%).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 12h;	4 Preparation of compound 4-1 After mixing 1-bromo-2-nitrobenzene (44 g, 0.21 mol), dibenzo[b,d]furan-4-yl boronic acid (40 g, 0.18 mol), Pd(PPh3)4 (10.3 g, 0.008 mol), K2CO3(72 g, 0.53 mol), toluene (880 mL), EtOH (300 mL) and distilled water (300 mL), the reaction mixture was stirred for 12 hours at 120°C. After terminating the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried with MgSO4, was filtered, was distilled under reduced pressure to remove the solvent, and was filtered through column to obtain compound 4-1 (43 g, 85 %).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 120℃; for 4h;	14 Dibenzo[b,d]furan-4-ylboronic acid 45 g (0.21 mol), 1-bromo-2-nitrobenzene 39 g (0.19 mol), Pd(PPh3)4 11.1g (0.0096 mol), K2CO3 (2M) 290mL, and ethanol 290 mL were put into a 1L two-neck RBF, and toluene 580mL was added thereinto. The resultant mixture was heated to 120 , and then stirred for 4 hours. Upon completion of the reaction, the resultant material was washed with distilled water, and extracted with ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed by a rotary evaporator, followed by purification using column chromatography, thereby obtaining Compound 14-1 47g (85%).
85%	Stage #1: 4-dibenzofurylboronic acid; 2-nitrophenyl bromide With potassium carbonate In tetrahydrofuran; water for 0.5h; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	1 Preparation of compound 1-1 After mixingl-bromo-2-nitrobenzene (39 g, 0.19 mol), dibenzo[b,djfuran-4-yl boronic acid (45 g, 0.21 mol), Pd(PPh3)4 (11.1 g, 0.0096 mol), 2 M K2C03 aqueous solution 290 mL, EtOH 290 mL, and toluene 580 mL, the reactant mixture was stirred for 4 hours while heated to 120°C. After the reaction is completed, the mixture was washed with distilled water, and extracted with EA. The extracted organic layer was dried with anhydrous MgSO4, and the solvent was removed with a rotary evaporator. The residue was purified by column chromatography to obtain compound 1-1 (47 g,
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	1 Preparation of compound 1-1 Preparation of compound 1-1[92]After mixing 1-bromo-2-nitrobenzene (39.0 g, 0.19 mol), dibenzo[b,d]furan-4-yl boronic acid (45.0 g, 0.21 mol), tetrakis(triphenylphosphine)palladium(O) (Pd(PPh3)4) (11.1 g, 0.0096 mol), aqueous 2M K2CO3solution (290.0 mL), ethanol (EtOH) (290.0 mL), and toluene (580.0 mL), the mixture was stirred for 4 hrs while heating to 120°C. Upon completing the reaction, the mixture was rinsed with distilled water and extracted with ethyl acetate (EA), the organic layer was dried with anhydrous MgSO4, the solvent was removed by using a rotary evaporator, and the obtained product was purified through column chromatography to obtain compound 1-1 (47.0 g, 85 %).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	5 Preparation of Compound 5-1 After mixing 1-bromo-2-nitrobenzene 39 g (0.19 mol), dibenzo[b,d]furan-4-yl boronic acid 45 g (0.21 mol), Pd(PPh3)4 11.1 g (0.0096 mol), 2 M K2CO3 aqueous solution 290 mL, EtOH 290 mL, and toluene 580 mL, the mixture was stirred while heating at 120° C for 4 hours. After completing the reaction, the mixture was washed with distilled water, extracted with EA, and the organic layer was dried with anhydrous MgSO4. Then, solvent was removed with a rotary evaporator, and the remaining product was purified using column chromatography to obtain compound 5-1 47 g (85%).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	5 Preparation of compound 5-1 1-Bromo-2-nitrobenzene (39.0 g, 0.19 mol), dibenzo[b,d]furan-4-yl boronic acid (45.0 g, 0.21 mol), Pd(PPh3)4 (11.1 g, 0.0096 mol), aqueous solution of 2M K2CO3 (290.0 mL), EtOH (290.0 mL), and toluene (580.0 mL) were mixed in a flask, heated to 120°C and stirred for 4 hrs. After completing the reaction, the mixture was washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by using a rotary evaporator. The organic layer was purified by column chromatography to obtain compound 5-1 (47.0 g, 85 %).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene for 24h; Reflux; Inert atmosphere;	2.2. Preparation of 4-(2-nitrophenyl)dibenzo[b,d]furan General procedure: Dibenzo[b,d]furan-4-ylboronic acid (10.00 g, 47.16 mmol), 1-bromo-2-nitrobenzene (7.94 g, 39.31 mmol), and tetrakis(-triphenylphosphine)palladium(0) (1.59 g, 1.38 mmol) were dissolvedin a solution of 2-M potassium carbonate (70 mL) andtoluene (200 mL). The reaction mixture was refluxed under nitrogenfor 24 h. The mixture was diluted with dichloromethane andwashed with distilled water. The organic layer was treated withanhydrous magnesium sulfate and evaporated in vacuo to yield thecrude product, which was purified by column chromatographyusing dichloromethane/n-hexane to obtain a yellow powder. Theresults are as follows:Yield 85%. 1H NMR (300 MHz, CDCl3) d 8.12e8.15 (m, 2H),7.82e7.84 (d, 1H), 7.64e7.61 (d, 1H), 7.58e7.51 (d, 1H), 7.49e7.41 (m, 3H), 7.35e7.31 (t, 3H). Mass (FAB) m/z 290 [(M1)]. Anal. Calcd.for C18H11NO3: C, 74.73%; H, 3.83%; N, 4.84%; O, 16.59%. Found: C,74.9%; H, 3.40%; N, 4.43%; O, 16.12%.
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 4h;	5 Preparation of Compound 5-1 39 g (0.19 mol) of 1-bromo-2-nitrobenzene, 45 g (0.21 mol) of dibenzo[b, d]furan-4-ylboronic acid, Pd (PPh 3) 4 11.1 g (0.0096 mol), 290 mL of 2M K2CO3 aqueous solution, 290 mL of EtOH and 580 mL of toluene were mixed and stirred for 4 hours while heating to 120 ° C. After the reaction, rinse with distilled water and extract with EA After drying over MgSO4, the solvent was removed with a rotary evaporator. After purification by column chromatography to give 47 g (85%) of compound 5-1.
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Reflux; Inert atmosphere;	2 Synthesis of Intermediate 6-1 In a three-necked flask,4-boronic acid-dibenzofuran (21 g, 0.1 mol) was added,O-bromonitrobenzene (20 g, 0.1 mol)Potassium carbonate (27.6 g, 0.2 mol)Tetraphenylphenylphosphine palladium (1 g),Tetrahydrofuran (300 mL) and water (100 mL),Heated under reflux under nitrogen for 12 hours,Cooled, extracted with dichloromethane, dried, filtered, concentrated,The mixture was stirred with methanol, filtered and dried to give 24 g, 84% yield.
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In tetrahydrofuran for 8h; Inert atmosphere; Heating;	1.1 1) Under a nitrogen atmosphere at 250mlDibenzofuran-4-boronic acid (S1) in a round bottom flask(2g) and 2-nitrobromobenzene(2g) completely dissolved inIn 60 ml of tetrahydrofuran,Add 4ml of 2M sodium carbonate solution,Then add tetrakis-(triphenylphosphine)palladium (0.2g),The mixture was stirred with heating for 8 hours.After going to room temperature,Remove the water layer.Add 100 ml of dichloromethane,It was washed twice with 30 ml of saturated brine.The dichloromethane layer was dried over anhydrous magnesium sulfate.Concentrate in vacuo.Then use petroleum ether:Ethyl acetate (20:1 to 2:1)Purified and separated as a eluent on a silica gel column.Obtaining S2 (yield 84%)
73.3%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 90℃; for 24h; Inert atmosphere;	17 Synthesis of intermediate M-17 In a round bottom flask in a nitrogen atmosphere of 500 material dibenzofuran Borough Nick Acid (15.0 g, 70.7 mmol), material 1-bromo-2-nitrobenzene (19.38 g, 77.83 mmol), and tetrakis triphenylphosphine palladium (2.46g, 2.12 mmol) was dissolved in 200 mL of toluene, potassium carbonate (19.56 g, 141 mmol), containing water 70 then was stirred at 90 ° C for 24 hours. The reaction is complete, the reaction was cooled to room temperature, and remove water and the reaction was extracted with water and toluene over anhydrous magnesium sulfate, and filtrated to remove the solvent. Removing the solvent and then methylene chloride / hexane (1: 1) mixed solvent and purified via a silica column Kell intermediate M-17 15 g (yield: 73.3%) was obtained.
69.2%	Stage #1: 4-dibenzofurylboronic acid; 2-nitrophenyl bromide In toluene Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; water; toluene at 120℃; for 24h;	In a 250ml three-neck bottle, under nitrogen protection,Add 0.05 mol of intermediate S1-1, 0.06 mol of raw material II-1,100ml of toluene, stirring and mixing, then adding 0.0025mol Pd(PPh3)4, 0.075mol potassium carbonate, 50ml water and ethanol 1:1The mixture was stirred and warmed to 120°C and refluxed for 24 hours.Sampling point plate, showing no intermediate S1-1 remaining, complete reaction;It was cooled to room temperature, filtered, and the filtrate was separated. The organic phase was centrifuged under reduced pressure until no fractions were collected. A neutral silica gel column was used to obtain intermediate S2-1. HPLC purity was 99.6%, and the yield was 69.2%.
69.2%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 120℃; for 24h; Inert atmosphere;	1 In a 250ml three-necked bottle, under nitrogen protection, Add 0.05 mol of intermediate S1-1, 0.06 mol of starting material II-1, 100 ml of toluene, Stir and mix, then add 0.0025mol Pd(PPh3)4, a mixture of 0.075 mol of potassium carbonate, 50 ml of water and ethanol 1:1, Stirring to 120 ° C, refluxing for 24 hours, sampling the plate, It shows that there is no intermediate S1-1 remaining, and the reaction is complete; Naturally cooled to room temperature, filtered, and the filtrate was layered. The organic phase is decanted by rotary distillation to a fraction without distillation, and passed through a neutral silica gel column.Intermediate S2-1 was obtained, the HPLC purity was 99.6%, and the yield was 69.2%;
67%	With sodium carbonate In 1,2-dimethoxyethane; water; toluene for 12h; Inert atmosphere; Reflux;	32.1 Compound 2-bromonitrobenzene (25.0 g, 123.8 mmol), 4-dibenzofuranboronic acid (31.5 g, 148.5 mmol), a 2 M aqueous solution of Na2CO3 (124 mL, 248 mmol), DME (250 mL), toluene (250 mL), and Pd [PPh3]4 (7.2 g, 6.2 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 12 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 24.0 g in 67% yield. FD-MS analysis C18H11NO3: theoretical value 289, observed value 289
67%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water; toluene for 12h; Inert atmosphere; Reflux;	2-4 INTERMEDIATE SYNTHESIS 2-4: Synthesis of intermediate 2-4 In an argon atmosphere, 124 ml (248 mmol) of a 2 M aqueous solution of Na2CO3, 250 ml of DME, 250 ml of toluene, and 7.2 g (6.2 mmol) of Pd[PPh3]4 were added to a mixture of 25.0 g (123.8 mmol) of 2-bromonitrobenzene, 31.5 g (148.5 mmol) of 4-dibenzofuranboronic acid. The resultant mixture was stirred for 12 h while refluxing under heating. [0171] After the reaction, the mixture was cooled to room temperature. The reaction product was added with 500 ml of water and extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, filtered, and concentrated. The concentrate was purified by silica gel column chromatography, to obtain 24.0 g of white solid, which was identified as the following intermediate 2-4 by FD-MS analysis (yield: 67%).
67%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; toluene for 12h; Inert atmosphere; Reflux;	Synthesis of Intermediate A 2-Bromonitrobenzene (25.0 g, 123.8 mmol) and 4-dibenzofuranboronic acid (31.5 g, 148.5 mmol) were mixed under a nitrogen atmosphere, and a 2M aqueous sodium carbonate solution (124 ml, 248 mmol) was mixed with this mixture. , 1,2-Dimethoxyethane (DME) 250 ml, toluene (250 ml), and tetrakis (triphenylphosphine) palladium (0) (Pd [PPh3] 4) (7.2 g, 6.2 mmol) to prepare a sample. Then, the mixture was heated under reflux and stirred for 12 hours.After the reaction was completed by heating, refluxing and stirring, the sample was cooled to room temperature. The sample cooled to room temperature was transferred to a separating funnel, 500 ml of water was added, and the sample was extracted with dichloromethane. The extracted sample was dried on sulfonyl4, filtered, and the filtrate was concentrated. The sample obtained by concentrating the filtrate was purified by silica gel column chromatography to obtain 24.0 g of a white solid. As a result of analysis by FD-MS, this white solid was identified as Intermediate A. (The yield of Intermediate A was 67%.)
12 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 80℃;	32 Synthesis of intermediate 32-1 In a 250 mL three-necked round bottom flask, 4-dibenzofuran-boronic acid (10 g), 1-bromo-2-nitrobenzene (11.8 g), toluene (100 mL), ethanol (20 mL), potassium carbonate (12.1 g) and water (20 mL) were added and stirred. Tetrakis(triphenylphosphine)palladium (0) (1.5 g) was added to this mixed solution, and it heated at 80 °C. The reaction solution was separated into layers to remove water, and the organic layer was washed twice with water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent. 12 g of the titled compound was obtained by column separation using a dichloromethane and hexane mixed solvent.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 80℃; for 3.5h;	2 In a reaction flask, 36 g (100 mmol) of M, 15.5 g (110 mmol) of 2-bromonitrobenzene,Tetrakis (triphenylphosphine palladium) 0.9 g (0.785 mmol, 0.5%), 1500 ml of toluene, 1000 ml of ethanol, 43.3 g (314 mmol) of potassium carbonate / 1000 ml of water, and react at 80 ° C for 3.5 h.When the reaction is complete, stop the reaction. After cooling to room temperature, the reaction liquid was separated, and the organic phase was concentrated. The obtained solid was filtered to obtain yellow powder M1.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 120℃; for 24h; Inert atmosphere;	1 In a 250 mL three-necked flask, add 0.01 mol of raw material M1, 0.012 mol of raw material N1, 150 mL of toluene and ethanol mixed solvent (including 100 mL of toluene and 50 mL of ethanol) under nitrogen protection, and then add 0.02 mol K2CO3, 1 × 10-4mol Pd (PPh3) 4, heated to 120 ° C, reacted for 24 hours under reflux, and the sampling point plate showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced pressure rotary evaporation (-0.09MPa, 85 ° C), the residue was passed through a neutral silica gel column to obtain intermediate a1
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene Reflux;
67 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water; toluene Inert atmosphere; Reflux;	1.1-1 Synthesis of Intermediate A Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (124 mL, 248 mmol), 1,2-dimethoxyethane (DME) (250 mL), toluene (250 mL), and tetrakis(triphenylphosphine)palladium(0) (Pd[PPh3]4) (7.2 g, 6.2 mmol) were added to 2-bromonitrobenzene (25.0 g, 123.8 mmol) and 4-dibenzofuran boronic acid (31.5 g, 148.5 mmol) and the obtained mixture was heated to reflux with stirring for 12 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO4, filtered and condensed. The obtained sample was purified by silica-gel column chromatography to obtain a white solid (24.0 g). The solid was identified as an intermediate A by analysis according to FD-MS (Field Desorption Mass Spectrometry) (a yield rate: 67%).
67 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water; toluene Inert atmosphere; Reflux;	1-1 Synthesis of Intermediate A Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (124 mL, 248 mmol), 1,2-dimethoxyethane (DME) (250 mL), toluene (250 mL), and tetrakis(triphenylphosphine)palladium(0) (Pd[PPh3]4) (7.2 g, 6.2 mmol) were added to 2-bromonitrobenzene (25.0 g, 123.8 mmol) and 4-dibenzofuran boronic acid (31.5 g, 148.5 mmol) and the obtained mixture was heated to reflux with stirring for 12 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO4, filtered and condensed. The obtained sample was purified by silica-gel column chromatography to obtain a white solid (24.0 g). The solid was identified as an intermediate A by analysis according to FD-MS (Field Desorption Mass Spectrometry) (a yield rate: 67%).

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2
[ 1246308-80-4 ]
[ 1199616-66-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triphenylphosphine In 1,2-dichloro-benzene for 36h; Reflux;
95%	With triethyl phosphite for 10h; Reflux;	2.3. Preparation of 5H-benzofuro[3,2-c]carbazole General procedure: 4-(2-Nitrophenyl)dibenzo[b,d]furan (10.00 g, 34.57 mmol) wasdissolved in triethylphosphite (100 mL) and refluxed for 10 h. Thereaction mixture was cooled to room temperature and extractedwith ethyl acetate and distilled water. The organic layer was treatedwith anhydrous magnesium sulfate, and the solvent was removedby rotary evaporation. Impurities were removed by column chromatographyon silica gel using dichloromethane/n-hexane toobtain a yellowish powder. The results are as follows:Yield 95%. 1H NMR (300 MHz, CDCl3) d 11.8 (s, 1H), 8.32e8.35 (d,1H), 7.82e7.84 (d, 1H), 7.64e7.61 (d, 1H), 7.58e7.51 (d, 1H),7.49e7.41 (m, 3H), 7.35e7.31 (t, 3H). Mass (FAB) m/z 257 [(M1)].Anal. Calcd. for C18H10NO: C, 87.36%; H, 3.93%; N, 5.47%; O, 6.24%.Found: C, 87.7%; H, 3.4%; N, 5.03%; O, 6.41%.
92%	With triphenylphosphine In 1,2-dichloro-benzene at 120℃;	16.3 Synthesis Example 16-(3): Intermediate 16-c In a 250-ml reactor, (10.4 g, 36 mmol) and triphenyl phosphine (17.9 g, 2 mmol) were placed, followed by 1,2-dichlorobenzene (80 ml). The reactor was heated to 120° C. at which stirring was conducted overnight. After completion of the reaction, the reaction mixture was concentrated by heating. Isolation and purification by column chromatography afforded . (8.5 g, 92%)

81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	5 Compound 5-1 (47g, 0.16mol), triethylphosphite 600mL and 1,2-dichlorobenzene 300mL were mixed, and the mixture was heated to 150°C and stirred for 12 hours. After termination of the reaction, unreacted triethylphosphite and 1,2-dichlorobenzene were removed using a distillation device, and the mixture was washed with distilled water and extracted with EA. The organic layer was dried with anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Subsequently, column chromatography purification was conducted, yielding Compound 5-2 (39g, 81%).
81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	14 Compound 14-1 47g (0.16mol), triethylphophite 600mL, and 1,2-dichlorobenzen 300mL were put in a 1L two-neck RBF. The resultant mixture was heated to 150 , and then stirred for 12 hours. Upon completion of the reaction, the solvent was distilled, followed by wash with distilled water and extraction with ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed by a rotary evaporator, followed by purification using column chromatography, thereby obtaining Compound 14-2 39g (81%).
81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	1 Preparation of compound 1-2 After mixing compound 1-1(47 g, 0.16 mol), triethylphosphite 600mL, and1,2-dichlorobenzene 300 mL, the reactant mixture was heated to 150°C and stirred for12 hours. After the reaction is completed, unreacted triethylphosphite and1 ,2-dichlorobenzene were removed using a distillation apparatus. The remainingmixture was washed with distilled water, and extracted with EA. The extracted organiclayer was dried with anhydrous MgSO4, and the solvent was removed with a rotaryevaporator. The residue was purified by column chromatography to obtain compound1-2 (39 g, 81%).
81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	1 Preparation of compound 1-2 Preparation of compound 1-2[94]After mixing compound 1-1 (47.0 g, 0.16 mol), triethyl phosphite (600.0 mL), and 1,2-dichlorobenzene (300.0 mL), the mixture was stirred for 12 hrs while heating to 150°C. Upon completing the reaction, unreacted triethyl phosphite and 1,2-dichlorobenzene were removed by using a distillation equipment. The residue was rinsed with distilled water and extracted with EA, and the organic layer was dried with anhydrous MgSO4. After removing the solvent by using a rotary evaporator, the obtained product was purified through column chromatography to obtain compound 1-2 (39.0 g, 81 %).
81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	5 Preparation of Compound 5-2 After mixing compound 5-1 47 g (0.16 mol), triethylphosphite 600 mL, and 1,2-dichlorobenzene 300 mL, the mixture was stirred at 150° C. for 12 hours. After completing the reaction, unreacted triethylphosphite and 1,2-dichlorobenzene was removed using a distillation apparatus, and the remaining product was washed with distilled water, extracted with EA, and the organic layer was dried with anhydrous MgSO4. Then, solvent was removed with a rotary evaporator, and the remaining product was purified using column chromatography to obtain compound 5-2 39 g (81%).
81%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 12h;	5 Preparation of compound 5-2 Compound 5-1 (47.0 g, 0.16 mol), triethylphosphite (600.0 mL), and 1,2-dichlorobenzene (300.0 mL) were mixed in a flask, heated to 150°C and stirred for 12 hrs. After completing the reaction, the unreacted triethylphosphite and 1,2-dichlorobenzene were removed by using a distillation device. The mixture was washed with distilled water and extracted with EA. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by using a rotary evaporator. The organic layer was purified by column chromatography to obtain compound 5-2 (39.0 g, 81 %).
81%	With triethyl borate In 1,2-dichloro-benzene at 150℃; for 12h;	5 Preparation of Compound 5-2 47 g (0.16 mol), compound 5-1, 600 mL of triethylphosphite and 300 mL of 1,2-dichlorobenzene After mixing the mixture was heated to 150 °C and stirred for 12 hours. After the reaction, the unreacted triethyl phosphite and 1,2-dichlorobenzene were removed using a distillation apparatus. After washing with distilled water and extracting with EA, the organic layer was dried over anhydrous MgSO4. The solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain 39 g (81%) of Compound 5-2.
78%	With triethyl phosphite at 90℃; for 12h;	4 Preparation of compound 4-2 After mixing compound 4-1 (43 g, 0.15 mol), P(OEt)3 (400 mL, 0.4 M) and triethylphosphite (400 mL), the reaction mixture was stirred for 12 hours at 90°C. After terminating the reaction, the reaction mixture was distilled to remove triethylphosphite, and was filtered through column to obtain compound 4-2 (30 g, 78 %)
77.8%	With triphenylphosphine In 1,2-dichloro-benzene at 170 - 190℃; Inert atmosphere;	1.1-2.2 Step 2: In a 250 mL three-necked flask, under nitrogen protection,Add 0.02 mol of intermediate S1-1 and dissolve with 100 mL of o-dichlorobenzene.Add 0.03 mol of triphenylphosphine and stir the reaction at 170-190 ° C for 12-16 h.After the reaction is completed, it is cooled to room temperature, filtered, and the filtrate is evaporated under reduced pressure to pass through a neutral silica gel column to obtain intermediate S2-1;HPLC purity 97.2%, yield 77.8%;
76%	With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 12h;	2 Weigh 0.01mol of intermediate a1 in 100mL of o-dichlorobenzene, add 1 × 10-4mol of triphenylphosphine, and react at 180 ° C for 12h. After the reaction is completed, cool to room temperature, filter, and spin-filter the filtrate. The residue was passed through a silica gel column to obtain intermediate II-1; HPLC purity of intermediate II-1 was 99.82%, yield 76.0%.
75%	With triphenylphosphine In dichloromethane at 170℃; for 24h;	13 Intermediate To a round bottom flask M-35 25g (86.4mmol), triphenylphosphine into the pin 45.3g (173mmol) dichlorobenzeneWas dissolved was added (260ml) it was stirred in 170 for 24 hours under a nitrogen atmosphere. After the reaction of toluene andThe extract was then extracted with distilled water and concentrated to dryness under reduced pressure and filtered through a magnesium sulfate, and the filtrate. The product n- hexaneAcid / dichloromethane (7: 3 by volume) as a silica gel column chromatography to give the desired compound of Photography the intermediate M-3716.7g (yield: 75%).
75%	With triphenylphosphine In 1,2-dichloro-benzene at 170℃; for 24h; Inert atmosphere;	2 Synthesis Example 2: Synthesis of Intermediate M-2 25 g (86.4 mmol) of Intermediate M-1 and 45.3 g (173 mmol) of triphenylphosphine were put in a round-bottomed flask, and 260 ml of dichlorobenzene was added thereto to dissolve them and then, stirred under a nitrogen atmosphere for 24 hours at 170° C. When a reaction was complete, an extraction solution obtained by performing an extraction with toluene and distilled water was dried with magnesium sulfate and filtered, and then, a filtrate therefrom was concentrated under a reduced pressure. A product therefrom was purified through silica gel column chromatography with n-hexane/dichloromethane (a volume ratio of 7:3) to obtain 16.7 g of Intermediate M-2 as a target compound (a yield=75%). (0130) LC-Mass (theoretical value: 257.08 g/mol, measured value: M+1=258.21 g/mol)
71%	With triethyl phosphite In neat (no solvent) at 150℃; for 5h;	4 Preparation of compound 95-4 [188] After dissolving compound 95-3 (126 g, 0.44 mmol) in triethylphosphite (1.1 L), the mixture was stirred for 5 hours at 150°C under reflux. The mixture was cooled to room temperature and distilled under reduced pressure. The crude product was purified through silica gel column chromatography and recrystallization to obtain compound 95-4 (80 g, 71 %).
71%	With triethyl phosphite at 150℃; for 5h; Reflux;	1 Preparation of compound C-98-4 4-(2-nitrophenyl)dibenzo[b,d]furan (compound C-98-3) 126g(0.44mol) was dissolved in triethylphosphite [P(OTe)3] 1.1L, and the mixture was then stirred under reflux at 150°C. After 5 hours, the mixture was cooled to room temperature, and then distilled under reduced pressure. The resultant solid was separated by silica gel column chromatography and recrystallization to obtain compound C-98-4 (80g, 71%).
71.5%	With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 12h; Inert atmosphere;	In a 250ml three-neck bottle, under nitrogen protection,Added 0.04 mol of intermediate S2-1, 0.05 mol of triphenylphosphine,100ml o-dichlorobenzene, stirring and mixing, heating to 180°C, reaction for 12 hours,Sampling point board showing no intermediate S2-1 remaining,The reaction is complete; it is naturally cooled to room temperature, filtered, and the filtrate is evaporated under reduced pressure to zero fraction.After neutral silica gel column, the intermediate M1-6 was obtained and HPLC purity was 99.7%.Yield 71.5%;
71.5%	With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 12h; Inert atmosphere;	1 In a 250ml three-necked bottle, under nitrogen protection, Add 0.04 mol of intermediate S2-1, 0.05 mol of triphenylphosphine, 100 ml of o-dichlorobenzene, stir and mix, heat to 180 ° C, and react for 12 hours. The sampling point plate shows that there is no intermediate S2-1 remaining, and the reaction is complete; It was naturally cooled to room temperature, filtered, and the filtrate was evaporated to dryness under reduced pressure. Through a neutral silica gel column, the intermediate M1-1 was obtained, the HPLC purity was 99.7%, and the yield was 71.5%;
70%	With triethyl phosphite In 1,2-dichloro-benzene Inert atmosphere; Reflux;	1.2 2) Under nitrogen atmosphere at 250mlS2 (6g) in a round bottom flaskAnd triethyl phosphite (16g)Completely dissolved in o-dichlorobenzene (120ml),Heat to reflux for 6-10 hours.O-dichlorobenzene (70-90 ml) was distilled off under reduced pressure.After cooling, pour into dilute hydrochloric acid,It was extracted twice with 30 ml of dichloromethane.The dichloromethane layer was dried over anhydrous magnesium sulfate.Concentrate in vacuo.Then use dichloromethane:Methanol (20:12:1) was purified and separated as a leaching agent on a silica gel column.Obtaining S3 (yield 70%)
70%	With triethyl phosphite In 1,2-dichloro-benzene Inert atmosphere; Reflux;	1.2 Under a nitrogen atmosphere at 250 mlIn a round bottom flask, S2 (6 g) and triethyl phosphite (16 g) were completely dissolved in o-dichlorobenzene (120 ml), and heated under reflux for 6-10 hours. O-dichlorobenzene (70-90 ml) was distilled off under reduced pressure, and the mixture was cooled, poured into dilute hydrochloric acid, and extracted twice with dichloromethane (30 ml). The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. Then, using dichloromethane:methanol (20:1 to 2:1) as a eluent to purify on a silica gel column to obtain S3 (yield 70%);
70%	In 1,2-dichloro-benzene at 160℃; for 12h; Inert atmosphere;	8 Synthesis of Compound 8-2 Compound 8-1 (13.00 g, 45 mmol) was added to a three-necked flask, stirred and dissolved with 150 mL of triethylphosphoric acid, and protected with nitrogen.Then, the mixture was heated to 160 ° C and stirred under reflux for 12 hours. The organic phase was distilled off under reduced pressure, and the residue was applied with DCM and water.The organic phase was combined, washed with saturated brine and dried over anhydrous sodium sulfate.The solvent was evaporated and the residue was crystallised from DCM /EtOAc.The yellow solid was obtained as Compound 8-2 (8.6 g, yield 70%).
68%	With triphenylphosphine In ISOPROPYLAMIDE for 20h; Reflux; Inert atmosphere;	32.2 Compound 50 (24.0 g, 83.0 mmol), triphenylphosphine (54.4 g, 207.4 mmol), and dimethylacetamide (166 mL) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 20 hours. After the completion of the reaction, the resultant sample was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (400 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 14.5 g in 68% yield. FD-MS analysis C15H11NO: theoretical value 257, observed value 257
68%	With triphenylphosphine In N,N-dimethyl acetamide for 20h; Inert atmosphere; Reflux;	2-5 INTERMEDIATE SYNTHESIS 2-5: Synthesis of intermediate 2-5 In an argon atmosphere, 166 ml of dimethylacetamide was added to a mixture of 24.0 g (83.0 mmol) of intermediate 2-4 and 54.4 g (207.4 mmol) of triphenylphosphine. The resultant mixture was stirred for 20 h while refluxing under heating. [0173] After the reaction, the mixture was cooled to room temperature. The reaction product was added with 400 ml of water and extracted with dichloromethane in a separatory funnel. The organic layer was dried over MgSO4, filtered and concentrated. The concentrate was purified by silica gel column chromatography, to obtain 14.5 g of white solid, which was identified as the following intermediate 2-5 by FD-MS analysis (yield: 68%).
68.2%	With triphenylphosphine In 1,2-dichloro-benzene for 24h; Inert atmosphere; Heating;	18 Synthesis of intermediate M-18 In a round bottom flask in a nitrogen atmosphere of 500mL M-17 (15.0 g, 51.8 mmol), triphenylphosphine (36 g, 137.5mmol) was dissolved in dichlorobenzene was stirred for 24 hours at 160 °C . After the cooling the reaction to room temperature reactionEach was was removed under reduced pressure dichlorobenzene. Silica with a solvent mixture: The reaction of methylene chloride / hexane (1: 1)The intermediate M-18 was purified via column Kell 9.1 g (yield: 68.2%) was obtained.
68%	With triphenylphosphine In 1,2-dichloro-benzene for 20h; Inert atmosphere; Reflux;	Synthesis of Intermediate B Under an argon atmosphereA sample was prepared by adding 166 ml of ortodichlorobenzene to a mixture of Intermediate A (24.0 g, 83.0 mmol) and triphenylphosphine (54.4 g, 207.4 mmol), and the mixture was heated under reflux and stirred for 20 hours. After completion of the reaction by heating under reflux stirring, the sample was cooled to room temperature. The sample cooled to room temperature was transferred to a separating funnel, 400 ml of water was added, and the sample was extracted with dichloromethane. The extracted sample was dried with sulfonyl4, filtered and concentrated. The sample was purified by silica gel column chromatography to obtain 14.5 g of a white solid. As a result of analysis by FD-MS, this white solid was identified as Intermediate B. (Revenue of intermediate BThe rate was 68%. )
67%	With 1,2-dichloro-benzene; triethyl phosphite for 12h; Reflux; Inert atmosphere;	2 Synthesis of Intermediate 6-2 In the flask,Intermediate 6-1 (10 g, 35 mmol) was added,O-dichlorobenzene (100 mL),Triethyl phosphite (50 mL),Heated under reflux under nitrogen for 12 hours, cooled,The solvent was removed under pressure and the crude product was purified by column chromatography to give 6 g,Yield 67%.
65%	With triphenylphosphine In 1,2-dichloro-benzene for 12h; Reflux;	Reaction Formula 10b 4-(2-nitrophenyl)dibenzo[b,d]furan 29.3 g (101.3 mmol) and triphenylphosphine 66.4 g (253.2 mmol) were dissolved in dichlorobenzene (210 mE). The mixture was refluxed/stirred for 12 hours. Afier completion of the reaction, dichlorobenzene was removed. The resultant was columned in a silica-gel and washed by methyl alcohol such that 5H-benzothro[3,2-c]carbazole (17 g, yield: 65%) was obtained.
63%	With triphenylphosphine In 1,2-dichloro-benzene for 48h; Inert atmosphere; Reflux;	1.3 3 Preparation of 5H-Benzofuro[3,2-c]carbazole): 4-(2-Nitrophenyl)dibenzo[b,d]furan (1 eq), triphenylphosphine (2.5 eq), 220 ml of o-dichlorobenzene,Drain N2 three times to ensure the system's oxygen-free environment, reflux for 48h,The system was brownish-black, the o-DCB was distilled off under reduced pressure, dichloromethane was dissolved, and the organic phase was washed three times with water, dried over anhydrous magnesium sulfate, filtered, and then passed to the column to obtain an off-white solid (63%).
63%	With triphenylphosphine In 1,2-dichloro-benzene for 48h; Inert atmosphere; Reflux;	4.3 (3) Preparation of 5-hydro-benzofuran [3,2-c]carbazole: 7.0 g of 4-(2-nitrophenyl)dibenzo[b,d]furan (24 mmol, 1 eq),15.7 g of triphenylphosphine (60 mmol, 2.5 eq) was added to a 500 ml three-necked flask.Add 220ml of o-dichlorobenzene and pump N2 three times to ensure the oxygen-free environment of the system.After refluxing for 48 h, the system was brownish black, and o-DCB was distilled off under reduced pressure.Wash the organic phase three times, dry and filter with anhydrous magnesium sulfate, mix the sample, and pass the column.Grayish solid5-hydro-benzofuran [3,2-c]carbazole3.9 g (yield 63%).
59%	With phenylmagnesium bromide In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; regioselective reaction;
52%	With triphenylphosphine In 1,2-dichloro-benzene for 18h; Reflux;	9 Preparation of compound 9-2 After mixing compound 9-1 (24 g, 83.0 mmol), PPh3 (65 g, 248.9 mmol) and 1,2-dichlorobebzene (250 mL), the reaction mixture was stirred for 18 hours under reflux. After terminating the reaction, the reaction mixture was cooled to room temperature, was washed with distilled water, and was extracted with dichloromethane (DCM). The extraceted DCM layer was washed with 5% NH4Cl aqueous solution, was dried with MgSO4, was filtered, was distillated under reduced pressure to remove the solvent, and was filtered through silica gel. The remaining solution was concentrated under reduced pressure, was triturated with MeOH to obtain compound 9-2 (11.2 g, 52 %).
37%	With triethyl phosphite In 1,2-dichloro-benzene at 150℃; for 24h;	1 After dissolving compound 1-2 (34 g, 117.5 mmol) in a mixture of P(OEt)3 (300 mL) and 1,2-dichlorobenzene (300 mL), the reaction mixture was stirred for 24 hours at 150°C. After terminating the reaction, the reaction mixture was concentrated under reduced pressure, was extracted with ethyl acetate (EA), and the organic layer was concentrated and purified through silica column to obtain compound 1-3 (11 g, 37 %).
	With triphenylphosphine In 1,2-dichloro-benzene at 170 - 190℃; Inert atmosphere;	1.b.2 (2) Under the protection of nitrogen, the intermediate S1 prepared in the previous step is dissolved in o-dichlorobenzene and triphenylphosphine is added.The reaction was stirred at 170-190 °C for 12-16 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, and the filtrate was evaporated under reduced pressure to give a neutral silica gel column. Intermediate S2 was obtained; the intermediate S1 and triphenylphosphine were molar. The ratio is 1:1~2;
	With triphenylphosphine In 1,2-dichloro-benzene at 170 - 190℃; Inert atmosphere;	1.b.2 (2) Under nitrogen protection, The intermediate S1 prepared in the previous step is dissolved in o-dichlorobenzene, Add triphenylphosphine, The reaction is stirred at 170-190° C. for 12-16 hours. After the reaction is completed, the reaction mixture is cooled to room temperature, filtered, and the filtrate is evaporated under reduced pressure. The intermediate S2 is obtained through a neutral silica gel column. The molar ratio of the intermediate S1 to triphenylphosphine is 1:1 to 2.
6 g	With triphenylphosphine In 1,2-dichloro-benzene for 12h; Reflux;	32 Synthesis of intermediate 32-2 Compound 32-1 (8 g), triphenylphosphine (20.6 g), 1,3-dichlorobenzene (56 mL) were added to a 250 mL three-necked round bottom flask, and the mixture was refluxed and stirred for 12 hours. The solvent was removed by concentration under reduced pressure. The resulting material was concentrated to give 5 g of the title compound by column separation using a dichloromethane, hexane mixed solvent.
	With triphenylphosphine In 1,2-dichloro-benzene for 1h; Inert atmosphere; Reflux;	2 Protect with N2, add 35g (100mmol) M1, add 17.7g triphenylphosphine (100mmol), 1000ml o-dichlorobenzene, heat and reflux for 12h, complete the reaction, evaporate the solvent, and silica gel column chromatography to obtain M2 intermediate.
	With triphenylphosphine In 1,2-dichloro-benzene at 180℃;

Reference： [1]Lee, Dong Ryun; Hwang, Seok-Ho; Jeon, Sang Kyu; Lee, Chil Won; Lee, Jun Yeob [Chemical Communications, 2015, vol. 51, # 38, p. 8105 - 8107]
[2]Gong, Myoung-Seon; Cha, Jae-Ryung; Lee, Chil Won [Organic electronics, 2017, vol. 42, p. 66 - 74]
[3]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - US2018/233669, 2018, A1 Location in patent: Paragraph 0345-0346
[4]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2012/39561, 2012, A1 Location in patent: Page/Page column 26; 27
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[6]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2016/18076, 2016, A1 Location in patent: Paragraph 89; 92; 93
[7]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2016/10380, 2016, A1 Location in patent: Paragraph 93-94
[8]Current Patent Assignee: DUPONT DE NEMOURS INC - JP2015/534547, 2015, A Location in patent: Paragraph 0145-0146; 0149-0150
[9]Current Patent Assignee: DUPONT DE NEMOURS INC - TW2016/5841, 2016, A Location in patent: Paragraph 0051-0052
[10]Current Patent Assignee: DUPONT DE NEMOURS INC - KR2019/84233, 2019, A Location in patent: Paragraph 0148; 0149; 0152; 0153
[11]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2013/12297, 2013, A1 Location in patent: Paragraph 122; 125; 126
[12]Current Patent Assignee: VALIANT CO., LTD. - CN110272427, 2019, A Location in patent: Paragraph 0085; 0097-0098; 0101-0102
[13]Current Patent Assignee: VALIANT CO., LTD. - CN110845393, 2020, A Location in patent: Paragraph 0089; 0091-0092; 0109; 0111
[14]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - KR2016/22081, 2016, A Location in patent: Paragraph 0526; 0527; 0528
[15]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2020/136057, 2020, A1 Location in patent: Paragraph 0128-0130
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[18]Current Patent Assignee: VALIANT CO., LTD. - CN107573354, 2018, A Location in patent: Paragraph 0052; 0053; 0058
[19]Current Patent Assignee: VALIANT CO., LTD. - CN109721619, 2019, A Location in patent: Paragraph 0044; 0052; 0057
[20]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN108948028, 2018, A Location in patent: Paragraph 0083; 0090; 0091
[21]Current Patent Assignee: ZHEJIANG HUAXIAN OPTOELECTRONICS TECHNOLOGY CO LTD - CN109053745, 2018, A Location in patent: Paragraph 0064; 0066; 0067; 0070; 0071
[22]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN109705018, 2019, A Location in patent: Paragraph 0283; 0284; 0286; 0287
[23]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2301926, 2011, A1 Location in patent: Page/Page column 138
[24]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2738166, 2014, A1 Location in patent: Paragraph 0172-0173
[25]Current Patent Assignee: SAMSUNG C&T CORPORATION - KR101486561, 2015, B1 Location in patent: Paragraph 0478-0481
[26]Current Patent Assignee: IDEMITSU KOSAN CO LTD - JP2021/20857, 2021, A Location in patent: Paragraph 0435; 0437
[27]Current Patent Assignee: SHANGHAI TAOE CHEMICAL TECHNOLOGY CO LTD; BAIKE BIOTECH (SHANGHAI) CO LTD - CN106892903, 2017, A Location in patent: Paragraph 0048; 0049; 0050; 003; 0054
[28]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2018/130953, 2018, A1 Location in patent: Paragraph 0222; 0223
[29]Current Patent Assignee: HUAZHONG UNIVERSITY OF SCIENCE & TECHNOLOGY - CN108285452, 2018, A Location in patent: Paragraph 0035; 0037; 0044; 0045
[30]Current Patent Assignee: WUHAN SHANGSAI OPTOELECTRONICS TECHNOLOGY CO LTD - CN109897029, 2019, A Location in patent: Paragraph 0063; 0064; 0068; 0069
[31]Gao, Hongyin; Xu, Qing-Long; Yousufuddin, Muhammed; Ess, Daniel H.; Kuerti, Laszlo [Angewandte Chemie - International Edition, 2014, vol. 53, # 10, p. 2701 - 2705][Angew. Chem., 2014, vol. 53, # 10, p. 2739 - 2743,5]
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3
[ 132-64-9 ]
[ 98-95-3 ]
[ 1246308-80-4 ]

Yield	Reaction Conditions	Operation in experiment
96.1%	With nickel trifluoromethanesulfonate; di-tert-butyl peroxide; 1,5-bis(2,6-dimethylphenyl)-2,4-pentanediimine; trifluoromethane sulfonic acid silver salt at 90℃; for 12h; Inert atmosphere;	1-29; 2 Example 4 Under nitrogen protection, 373.0g of nitrobenzene (99%, 3.0mol), 51.0g of dibenzofuran (99%, 0.3mol) were added to a 1000mL reaction flask,5.4g nickel triflate (99%, 0.015mol), 3.9g silver triflate (99%, 0.015mol), 13.9g ligand L2 (99%, 0.045mol),90.3g of di-tert-butyl peroxide (97%, 0.6mol), after feeding, was heated to 90°C,Stirring speed 600rpm, insulation reaction 12hr, after the reaction finishes,The unreacted nitrobenzene was recovered by distillation under reduced pressure, and water and ethyl acetate were added to the residue for extraction.The organic layer was desolvated to obtain the crude product, which was crystallized with ethanol to obtain 83.7 g of 4-(2-nitrophenyl)dibenzo[b,d]furan with a content of 99.6% and a yield of 96.1%.

Reference： [1]Current Patent Assignee: SINOSTEEL GROUP NANJING NEW MATERIAL RES INSTITUTE - CN113999196, 2022, A Location in patent: Paragraph 0018-0019; 0029-0086; 0090-0092

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