9-Bromo-10-(2-naphthyl)anthracene

off-white powder

9-Bromo-10-(naphthalen-2-yl)anthracene (Compound 1) 3.36 g (10 mmol) of 9, 10-dibromoanthracene and 1.72 g (10 mmol) of Intermediate-1 were introduced under nitrogen and dissolved in 40 ml of toluene0.58 g (0.5 mmol) of Pd (PPh3) 4 and 15 ml (30 mmol) of 2M K2CO3 were added, respectively, and refluxed for 24 hours.After completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H2O were added to extract the MC layer, Dried over MgSO4, concentrated, and then subjected to column chromatography with Hex: EA = 4: 1 to obtain Intermediate-7 2.45 (64percent).Synthesis of 9-bromo-10-(naphthalen-2-yl)anthracene 2 - 5 g of 9, 10 - 50 ml of dimethoxyethane [jiburomoantorasen[jiburomoantorasen]naphthalene boron acid 2.1 g of commercially available and dissolved, was heated to 80 °C. 50 ml distilled water and sodium carbonate 10 g was placed therein. Further thereto was 0.4 g (0) tetrakistriphenylphosphine. 3 hours after the separatory funnel by extraction with toluene, silica (SiO2) Synthesis of compound of the following formula 9-B[265] [Formula 9-B][266][267] The compound of the formula 9-A (5 g, 16.4 mmol) was added to dimethyl- formamide (160 mL), and N-bromosuccinimide (2.9 g, 16.4 mmol) was slowly added thereto. The mixture was stirred for 1 hour at normal temperature. The resulting precipitate was filtered to prepare a compound of the formula 9-B (6 g, yield 95percent).[268] MS: [M+H]9-(2-Naphthyl)anthracene (2.7 g, 8.9 mmole) was suspended in anhydrous N, N-dimethylformamide (DMF) (50 ml). The compound (6) 13.15 g (43.2 mmol) and NBS 8.48 g(47.5 mmol) were put into the chloroform 400 mL and itmixed reflux for 6 hours. The reaction solution was washed with the water 400 mL after doing the cooling in aroom temperature and it filtered to the Magnesium Sulfate Anhydrous. The residue was melted with chloroformafter concentration under reduced pressure is performed to the filter liquor and it recrystallized to the methanol and it dried and the compound (7) 15.42 g (yield 93percent) was obtained with filtering.Step 3 of the process can be illustrated by the preparation of 9-bromo-10-(2-naphthyl)anthracene in the following manner. 9-(2-Naphthyl)anthracene (14 g, 48 mmol, 1 eq) and N-bromosuccinimide (8.9 g, 50 mmol, 1.05 eq) were combined with 140 ml CHb. Preparation of Intermediate B9-naphthalen-2-yl-anthracene (Compound A, 15 g, 0.049 mol) was dissolved in methylene chloride (600 ml) in a 3-necked round-bottomed flask. BrRound bottom flask was added the intermediate (A) 14g (45.99mmol), NBS 9.00g (n-bromosuccinimide, 50.59mmol) and the mixture DMF (dimethylformamide 194ml) and the mixture was dissolved after stirring. Reflux and stirred for 12 hours under a nitrogen atmosphere. After the reaction was concentrated to filter the solid precipitate after poured into the DIW (delonized water), dried 5L, and the extract was filtered and then extracted with methylene chloride, dissolved magnesium sulfate, and the filtrate under reduced pressure. The product n- hexane / dichloromethane (7: 3 by volume) to give the silica gel column chromatography to give the intermediate (B) as 16g (90percent yield).Intermediates (A) to a round bottom flask was charged 14g (45.99mmol), into the NBS (n-bromosuccinimide) 9.00g (50.59mmol)Was dissolved was added to DMF (194ml) it was stirred. Reflux and stirred for 12 hours under a nitrogen atmosphere. The end of the reactionAfter the DIW (deionized water) filter after the solid precipitate was poured in 5L and the extract after the extraction dissolved in methylene chloride Filtered and concentrated and dried over magnesium sulfate and the filtrate under reduced pressure. The product n- hexane / dichloromethane (7: 3Volume ratio) to obtain a silica gel column chromatography to give the target compound as an intermediate (B) to 16g (90percent yield) andPut 250ml 3-necked flask, the compound D 9g (29.57 mmol) is dissolved in chloroform to put 108ml.After cutting off the light behind the glassware wrapped in aluminum foil, N- bromo-succinimideAdd the 7.37g (41.40 mmol).Groping water Quantize the reaction after 2 hours, Got, the structure: by extraction with chloroform, the compound E (9.65 g 85percent, yield).H1-NMRIt was confirmed by gyeokryeokc. Preparation of Intermediate D; 9-(Naphthalen-2-yl)-anthracene, compound C, (30 g, 98.56 mmol) was suspended in 300 mL DCM, followed by the addition of NBS (18.4 g, 103.38 mmol) to the flask. The mixture was refluxed under N(ii) Synthesis of 9-bromo-10-(2-naphthyl)anthracene; A synthesis scheme of 9-bromo-10-(2-naphthyl)anthracene is shown in (F-2). [0309][0310] 5.6 g (18.0 mmol) of 9-(2-naphthyl)anthracene and 90 mL of carbon tetrachloride were put into a 500-mL three-neck flask and stirred. A solution in which 3.2 g (20 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped into the above solution through a dropping funnel. After that, the solution was stirred at the room temperature for 1 hour, and a sodium thiosulfate aqueous 1000 mL three-necked flask, to a dropping funnel (dropping funnel) to install three-necked flask, the compound B (21 g, 69.00mmol) and DMF (400 mL) into the dropping funnel there NBS (19 g, 103.50 mmol) in DMF ( It was placed in a solution of 100 mL). When increasing the temperature is 60 the NBS solution is then made to fall one by one drop per second, all of the NBS solution drops and stirred for a further 4 hours. Then, water was added in order to terminate the reaction in an ice water bath. The solution was filtered with a glass filter, and then filtered, washed several times with water and finally washed with ethanol and dried. Using a hexane / toluene eluent was purified by column chromatography. Compound C (21.10 g, yield: 79.8percent) was obtained the, structure was confirmed by 1H-NMR.9-(2-naphthyl)-anthracene (7.36 g, 24.2 mmol) was dissolved in chloroform (150 mL), acetic acid (150 mL) was added thereto, and Br9-(2-naphthyl)-anthracene (7.36g, 24.2mmol) was dissolved in chloroform (150mL), afteraddition of acetic acid (150mL), Br2 (1.3mL, 25.4mmol ) was added dropwise at 0?, and the resulting mixture was stirred at room temperature for 5 hours. Afterthe reaction was completed, the reaction mixture was concentrated andrecrystallized with ethanol to obtain compound B-1 (6.49g, yield 70percent).(2) Synthesis of compound <6b>Under nitrogen atmosphere, 9-naphthalene-2-yl anthracene of 16.4g (54.0mmol) was melted by methylene chloride of 105OmL and slowly added with N.B.Sof 12.45g (70 mmol) which was melted by methylene chloride of 55OmL at 5 To a solution of 9-(2-naphthyl)anthracene (1.89 g, 6.24 mmol) as prepared in the 9-naphthalen-2-yl-anthracene (2.6g) by the dimethylformamide(26ml) solvent with N-bromosuccinimide bromide(4.6g) (bromination) acid is stirred for 4 hours at room temperature under mild condition to give 9-bromo-10-naphthalene-2-yl-anthracene (3.0g).

Molecular Weight:383.3
XLogP3:8
Rotatable Bond Count:1
Exact Mass:382.03571
Monoisotopic Mass:382.03571
Heavy Atom Count:25
Complexity:435
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes