2,7-Dibromo-9,10-phenanthrenedione

light yellow solid

3 grams of phenanthrene-9, 10-diketone (manufactured by Aldrich Co., 95percent) was dissolved in 60 ml HBr and 20 ml HUnder a nitrogen atmosphere, 41.64 g (200 mmol) of 4a, 10a-dihydro-9, 10-phenanthrenequinone was dissolved in 500 ml of anhydrous carbon tetrachloride, 3.28 g (20 mmol) of azobisisobutyronitrile was added at -70 ° C, Then, 78.31 g (440 mmol) of NBS was added in four portions. The temperature was maintained and the reaction was continued for 5 hours.The reaction is completed, washed with distilled water, extracted with carbon dioxide, dried over anhydrous sodium sulfate, distilled under reduced pressure, Purification by column chromatography gave 62.22 g, (170 mmol) of Intermediate E in 85percent yield.N-bromosuccinimide (19.6 g, 110 mmol) was added with smallportion to a solution of phenanthrene-9, 10-dione (1) (10.4 g, 50 mmol) in 500 ml of concentrated sulfuric acid and the mixturewas stirred overnight at room temperature. The reaction wasstopped by pouring into sufficient quantity of ice and then the solidcompound was filtered. The orange powder was washed withwater several times. Recrystallization from dimethyl sulfoxide(DMSO) gave the product as needle-like red crystals. (yield: 11.3 g, 63percent).1H NMR (DMSO-d6, 400 MHz) δ= 7.93 (d, 2H), 8.05 (d, 2H), 8.23 (d, 2H).A solution of 9, 10-phenanthrenequinone (20.8 g, 100 mmol) and concentrated sulfuric acid (300 ml) was added to a 500 ml three-necked round bottom flask and mechanically stirred for 15 minutes. Bromosuccinimide (NBS) (40 g, 220 mmol ).The reaction was carried out in the dark for 24 hours. After the completion of the reaction, the reaction was slowly poured into ice water, and the residue was washed several times with aqueous sodium bicarbonate, water and methanol.The residue was dried and rinsed with N, N-dimethylformamide (DMF) to give 22 g of an orange solid in 60percent yield.a) 104 g (0.50 mol) of 9, 10-dioxophenanthrene are suspended under nitrogen in 2000 ml of sulfuric acid and treated in small portions with a total of 182.5 g (1.03 mol) of N- bromosuccinimide during one hour at a temperature below 40°C. The resulting red brown viscous reaction mass is stirred at room temperature for four hours. The reaction mixture is slowly dropped into 6000 ml of an ice-water mixture under slow stirring. The resulting or-ange suspension is filtered and the solid washed with 5000 ml of water and 2000 ml of eth- anol, and then dried under vacuum at 70°C. The orange solid is dissolved in 2100 ml N, N- dimethylformamide (DMF) under reflux and further stirred at 80°C for one hour. The resulting suspension is filtered at 80°C and the solid washed with 1000 ml of DMF and 600 ml of methanol, followed by drying under vacuum at 80°C, giving the title product as a red powder (yield: 96.8 g (53percent)). Melting point: 284-285°C.Synthesis of Compound 15-1 In the three-necked flask, Is addedPhenanthrenequinone(6 · 24g, 30mmol), concentrated sulfuric acid (50ml), at 0 ° C and slowly added NBS (11.2g, 63mmol), 2 hours reaction, the reaction mixture was slowly poured into ice water, filtered, the cake washed with dimethylsulfoxide recrystallization sulfoneOrange solid 5.6g, 50percent yield.

Molecular Weight:366.00
XLogP3:3.9
Hydrogen Bond Acceptor Count:2
Exact Mass:365.87141
Monoisotopic Mass:363.87345
Topological Polar Surface Area:34.1
Heavy Atom Count:18
Complexity:346
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes