4-BroMo-9H-carbazole

2-Bromo-2'-nitro-1, 1'-biphenyl (4.7 g, 16.9 mmol) and triphenylphosphine (11.08 g, 42.25 mmol) were dissolved in 1, 2-dichlorobenzene (110 ml). [283] In a 250 ml round-bottom three-neck flask under a nitrogen atmosphere, 7.2 g of Intermediate 22, 6.8 g of triphenylphosphine and 160 ml of o-dichlorobenzene were placed, and stirred at 180°C for 18 hrs. The reaction solution was concentrated and then subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane, thus obtaining 2.6 g of Intermediate 24 (yield 86percent). [284] MS (ESI): [M+H]+ 2462-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in triphenylphosphine ( 4.5 g , 0.017 mol ) 1, 2-dichlorobenzene 100 mL was reacted with stirring for 24 hours at 180 . After the reaction cooled to H20: cheungbun the MC Li after columnpurification ( n - Hexane : MC ) to give the intermediate 20-1 4.2 g ( yield83percent)2-Bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in triphenylphosphine (4.5 g, 0.017 mol)in 1, 2-dichlorobenzene 100 mL into a 180 ° C at the 24-hour reaction was stirred.After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 2-1 4.2 g (yield 83percent)2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in 1, 2-dichlorobenzene 100 mL put to triphenylphosphine (4.5 g, 0.017 mol) was reacted with stirring for 24 hours at 180 . After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 7-1 4.2 g (yield 83percent) (m / z = 246).2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in triphenylphosphine (4.5 g, 0.017 mol) in 1, 2- Put dichlorobenzene 100 mL was reacted with stirring for 24 hours at 180 . After the reaction cooled to H20: cheungbun the MC Li after column purification (n-Hexane: MC) to give the intermediate 17-1 4.2 g (yield 83percent)2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in 1, 2-dichlorobenzene 100 mL put to triphenylphosphine (4.5 g, 0.017 mol) was reacted with stirring for 24 hours at 180 °C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to give the intermediate 31-1 4.2 g (yield 83percent)2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) in 1, 2-dichlorobenzene 100 mL put to triphenylphosphine (4.5 g, 0.017 mol) was reacted with stirring for 24 hours at 180 degree . After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 7-1 4.2 g (83percent yield).2-bromo-2'-nitrobiphenyl put 1, 2-dichlorobenzene in 100ml triphenylphosphine (4.5g, 0.017mol) in (5.0g, 0.017mol) was reacted by stirring for 24 hours stirring 180 °C. After the reaction cooled to H2O: After layer separation the MC column purification (n-Hexane: MC) to give the intermediate 50-1 4.2g (yield 83percent) (m / z = 246).2-bromo-2'-nitrobiphenyl (5.0g, 0.017mol), triphenylphosphine (4.5g, 0.017mol) put in 1, 2-dichlorobenzene 100ml, this mixture was reacted with stirring for 24 hours at 180 °C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 1-8 4.2g (83percent yield).2-bromo-2'-nitrobiphenyl in 1, 2-dichlorobenzene (5.0g, 0.017mol) in triphenylphosphine (4.5g, 0.017mol) Insert a 100ml reaction was stirred for 24 hours at 180 . After the reaction cooled to H20: After layer separation the column purification MC (N-Hexane: MC) to yield 4.2g of intermediate 13-1 (83percent yield)Synthesis method of intermediate 6; A compound 5 dissolved in orthodichlorobenzene, and triphenylphosphinepalladium were added in 2-neck, followed by refluxing and stirring for 24 hours. Then, the color of solvent was changed from yellow to brown. The resultant product was concentrated by raising the temperature up to room temperature, and then purified by silica gel column chromatography to give an intermediate 6 with a yield of 75percent.A 1 L reactor was charged with intermediate 5-b (30.7 g, 110 mmol), Triphenylphosphine (50.1 g, 330 mmol) was added to a solution of Dichlorobenzene (300 mL), and the mixture is refluxed for 24 hours.After completion of the reaction, the reaction mixture was concentrated and then subjected to column chromatography to obtain Intermediate 5-c (20.4 g, 75percent).Under an argon atmosphere, 38.6g (147 mmol) of triphenylphosphine, 16.3g (58.8 mmol) of M-7, and 65 mL of dichlorobenzene were placed in a three-necked flask. The mixture was heated under reflux while stirring for 18 hours. The reaction mixture was cooled to room temperature and purified by silica-gel column chromatography to obtain 9.4g of 4-bromocarbazole (yield: 65percent).To a 250 mL 2-neck round bottom flask was added intermediate 6-1 (100.0 mmol, 27.8 g) Triethylphosphite (700.0 mmol, 116.3 g) was added and refluxed at 160 ° C for 12 hours. The temperature of the reaction solution was lowered to room temperature and extracted with ethyl acetate. The resulting extract was dried over MgSO4 and then dried under reduced pressure to obtain a crude product. The filtrate was separated and purified by silica gel column chromatography to obtain 15.5 g (yield: 63percent) of Intermediate 6-2 as a yellow solid.To a 250 mL 2-neck round bottom flask was added intermediate 6-1 (100.0 mmol, 27.8 g)Triethylphosphite (700.0 mmol, 116.3 g) was added to a solution ofAnd refluxed at 160 ° C for 12 hours.The temperature of the reaction solution was lowered to room temperature and extracted with ethyl acetate. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain crude product. The crude product was separated and purified by silica gel column chromatography to obtain 15.5 g (yield: 63percent) of Intermediate 6-2 as a yellow solid.250ml round bottom flask in intermediate 12-a> (14.0g, 0.050mol), triphenylphosphine (33.01g, 0.126mol), N, N- dimethylacetamide (100ml) was stirred for 14 hour at 180°. When the reaction is complete, after cooling to room temperature, poured into water and stirred 200ml. Extraction with ethyl acetate and concentrated under reduced pressure to separate an organic layer. By column separation intermediate 12-b> (7.0g, 56.5percent) was obtained.250ml round bottom flask in (14.0g, 0.050mol), Triphenylphosphine (33.01g, 0.126mol), N, N- dimethyl-acetamide (100ml)The mixture was stirred 14 hours at 180 put. When the reaction is complete, after cooling to room temperature, poured into water and stirred 200ml. Extraction with ethyl acetate and concentrated under reduced pressure to separate an organic layer. Separated by column chromatography (7.0g, 56.5percent) was obtained.2′-bromo-2-nitro-biphenyl(7 g, 26 mmol), triphenylphosphine (16.7 g, 65 mmol) were added to60 mL of anhydrous 1, 2-diclorobenzene solution in 3-neck roundbottom flask under N2 atmosphere. The mixture was refluxed at 180 °Cfor 10 h (3.0 g, Yield 50percent) 1H NMR (300 MHz, THF): δ(ppm) 10.58 (s, 1H), 8.65–8.62 (d, 1H), 7.45–7.36 (m, 3H), 7.31–7.29 (d, 1H), 7.23–7.15 (m, 2H).Under argon atmosphere, a mixture of 20g (72 mmol) of the intermediate 1-1, 18.9 g (72 mmol) of triphenylphosphine, and 100 mL of o-dichlorobenzene was heated at 180 degrees C for eight hours while being stirred. Waterwas added to the reaction solution to precipitate solid. Then, the obtained solid was filtrated. The obtained solid waspurified by silica-gel column chromatography, so that the intermediate 1-2 (8.4 g, a yield of 47percent) was obtained.Under an argon gas atmosphere, a mixture of the intermediate 8-1 (20 g, 72 mmol), triphenylphosphine (18.9 g, 72 mmol) and o-dichlorobenzene (100 mL) was heated with stirring at 180 degrees C. for eight hours. Water was added to the reaction solution to precipitate solid. Then, the obtained solid was filtrated. The obtained solid was purified by silica-gel column chromatography, so that the intermediate 8-2 (8.4 g, a yield of 47percent) was obtained.Into the compound (128-a) 15.3g (55mmol), triphenylphosphine 36.1g (137.5mmol), o- dichlorobenzene (o-DCB) in 500mL reaction vessel was 15 hours at 185 under an argon atmosphere. after the completion of the reaction, dilute the residue obtained by distilling off the solvent under reduced pressure with toluene, and filtered to give precipitates, silica gel column chromatography (hexane: toluene = 1: 1 to 1: 3) to give, as a white to obtain a solid compound (128-b). 6.1g yield, the yield was 45percent.

Molecular Weight:246.10
XLogP3:4.6
Hydrogen Bond Donor Count:1
Exact Mass:244.98401
Monoisotopic Mass:244.98401
Topological Polar Surface Area:15.8
Heavy Atom Count:14
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes