9-BroMo-10-(1-naphthyl)anthracene

Off-white powder

In a 2-L 4-neck round-bottom flask, Intermediate 5-a (88 g 0.29 mol) was dissolved in dimethylformamide (700 mL). Thereafter, a solution of NBS (70.7 g, 0.4 mole) in dimethylformamide (200 ml) was slowly added, followed by stirring for 2 hrs. After completion of the reaction, the reaction mixture was mixed with water to precipitate Intermediate 5-b (108 g, 97.5percent).The [Reaction Scheme 15] is stirred into a (50 g, 205 mmol) and dimethylformamide 500 mL obtained from.The N- bromosuccinamide (36.5 g, 205 mmol) dividing the solid into the reactor and stirred for 3 hours at room temperature.The reaction was poured into a large amount of H2O, and filter the precipitated solid. To the slurry, and drying the filtered solid with methanol to give the 60.7 g. (92percent yield)In a 1 L reactor, add 50 g (205 mmol) of and 500 mL of dimethylformamide and stir. 36.5 g (205 mmol) of N-bromo-ricinamide was added to the reactor in a solid state, followed by stirring at room temperature for 3 hours.The reaction is poured into excess H2O and the precipitated solid is filtered.The solid was slurried with methanol and then filtered and dried to obtain 60.7 g of (yield: 92percent).Into the intermediates (E) 18g (70.77mmol), NBS 13.85g (77.85mmol) in a round bottom flask and stirred were dissolved was added to DMF (283ml). It was stirred under reflux for 24 hours under a nitrogen atmosphere. After the reaction was concentrated to a solids filter after precipitation was poured in 5L DIW, dried and filtered to extract 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 (F) as 21.23g (90percent yield).Intermediate (E) 18g (70.77mmol) in a round bottom flask, placed into the NBS 13.85g (77.85mmol) was dissolved was added to DMF (283ml)After the mixture was stirred. It was stirred under reflux for 24 hours under a nitrogen atmosphere. After the reaction was poured into precipitation in 5L DIWAfter the solid and dried filter, and the filtered extract was then extracted with methylene chloride, dissolved magnesium sulfate, and the filtrateIt was concentrated under reduced pressure. The product n- hexane / dichloromethane (7: 3 by volume) as purified by silica gel column chromatographyBy the intermediate of the desired compound (F) to give a 21.23g (90percent9-Naphthalen-1-yl-anthracene (2.3 g, 7.56 mmol) was dissolved in DMF (30 mL), and the solution was stirred. NBS (N-Bromosuccinimide) (1.48 g, 8.32 mmol) was added thereto, and the mixture was stirred. After 30 minutes, and thus completion of the reaction, water (H9-Naphthalen-1-yl-anthracene (2.3 g, 7.56 mmol) was dissolved in DMF (30 mL), and the solution was stirred. NBS (N-Bromosuccinimide) (1.48 g, 8.32 mmol) was added thereto, and the mixture was stirred. After 30 minutes, and thus completion of the reaction, water (H9-naphthalen-1-yl - anthracene 2.3g of (7.56 mmol) was dissolved in DMF (30mL) stirred with NBS (N-Bromosuccinimide) 1.48g (8.32mmol) . After 30 minutes, when the reaction is complete, water was added, after obtaining the precipitate by adding a small amount of ethanol, subjected to vacuum filters, compound 5b of off-white vacuum dried (2.6g, 89percent) It was obtained.The compound (3) 9.70 g (31.9 mmol) and NBS 6.25 g(35.1 mmol) were put into the chloroform 300 mL and itmixed reflux for 3hours. The reaction solution was washed with the water 300 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 was dry and the compound (4) 10.66 g (yield 87percent) was obtained with filtering.Next, 14.2 g (46.7 mmol) of compound (90) was dissolved in a mixed solvent of 400 mL of chlorobenzene (C9, 10-Dibromo anthracene(5.04g, 15mmol), naphthalene1-boronic acid (1.72g, 10mmol), Pd (PPh3) 4 ([0344] 0.58 g, 0.5mmol), potassium carbonate (4.15g, 30mmol) and THF: H2O = 2: 1 solution was dissolved in 200ml At 80 was stirred for 2 hours under reflux. Thereafter 40ml H2O was added and the organic layer was dried 40ml ether obtained by extraction three times with magnesium sulfate, and the intermediate B-3 to the residue obtained by evaporation of the solvent purification by silica gel column chromatography (3.06g, 80percent yield ) it was obtained.In NUnder a nitrogen atmosphere, 500mlThree-neck flask 1-naphthalene boronic acid (7g, 0.0407mol) and 9, 10-dibromo-anthracene (17.8g, 0.0529mol) for installation into a rear oil bath behind a 2M K2CO3 dissolved in THF and the solvent reflux sikimyeo 50 maintaining the temperature rises to Pd (PPh3) 4 catalyst 0.3g put back 80 ~ 90 temperature to sikimyeo allowed to react for about 16 to 24 hours. Extracted with dichloromethane (300ml), followed by the removal of water on the obtained organic extracts. Then, the solvent was evaporated, and to the organic phase, and separated by column chromatography using hexane-zero eluted G compound (9.7g, yield: 62.1percent) was obtained the, structure was confirmed by 1H-NMR.3.36 g (10 mmol) of 9, 10-dibromoanthracene and 1.72 g (10 mmol) of Intermediate-2 were introduced under nitrogen and dissolved in 45 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 columned with Hex: MC = 3: 1 to yield Intermediate-8 2.38 (62percent).Synthesis of 9-bromo-10-(naphthalen-1-yl)anthracene

9-Bromo-10-(1-naphthyl)anthracene is a heterocyclic organic substance and can be used as a pharmaceutical intermediate.

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