3-Bromo-9,10-phenanthrenedione

1000-ml, 45.0 g (0.216 mol) of phenanthrenequinone (Sub 1-1) was added to a four-neck round bottom flask, 400 ml of nitrobenzene and 0.52 g (2.16 mmol) of benzoyl peroxide were added and stirred. 12.18 ml (0.238 mol) of bromine was slowly added thereto.The reaction solution was irradiated with light with a 200 W tungsten lamp to conduct photoreaction for 3 hours.The reaction solution was cooled to room temperature, vacuum filtered, washed with methanol, and the resulting solid was separated and stirred in methanol.The solid was vacuum-dried again by vacuum filtration to obtain 64.3 g (yield: 82%) of Sub 7-1.To 41.6g (0.20 mol) of 9, 10-dioxo-phenanthrene was suspended under nitrogen in 500ml of acetic acid and 106 with 2.4g (0.01 mol) of dibenzoyl peroxide, whereafter in 75 minutes during the dropwise added 35.2g (0.22 mol) of bromine.During the addition was added dropwise over 75 minutes 35.2g (0.22 mol) of bromine was used during the addition was added dropwise over 45 minutes 25.6g (0.16 mol) of bromine.The reaction mixture was heated at 106 additional three hours, followed by stirring at room temperature for 20 hours.The yellow suspension was filtered, washed with a small amount of acetic acid, followed by washing with 500ml water and 500ml of ethanol.The remaining yellow solid (80g) was dissolved in hot N, N- dimethylformamide (DMF), and the solution was cooled to room temperature, until precipitation begins.The precipitate by stirring at room temperature for 1 hour to complete.The precipitated solid was filtered, washed with a small amount of methanol and DMF and the additional amount of hexane.At 50 deg.] C under vacuum to give a yellow powder after drying the title product (Yield: 34.8g (61%)).A compound A (9.25 g, 44.4 mmol) was charged in a 100 mL Schlenk tube, and then 20 mL of nitrobenzene was added thereto. Then, benzoyl peroxide (0.39 g, 1.61 mmol) was added thereto, and bromine (2.29 mL, 44.4 mmol) was added thereto dropwise. Then, the resultant was stirred while conducting heating for 4 hours at 60 C. Methanol was added to the resultant solution to precipitate a solid, and the solid was removed therefrom by filtration. The resulting solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a yellow solid (yield amount: 3.02 g, yield: 24%).Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 8.22 (dd, J=7.6, 1.6 Hz, 1H), 8.18 (d, J=1.6 Hz, 1H), 8.06 (d, J=8.4 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.75 (td, J=7.6, 1.2 Hz, 1H), 7.62 (dd, J=8.4, 2.0 Hz, 1H), 7.53 (t, J=7.6 Hz, 1H). It was confirmed by 1H NMR measurement that the obtained compound was a compound B.Step 3 :

Molecular Weight:287.11
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Exact Mass:285.96294
Monoisotopic Mass:285.96294
Topological Polar Surface Area:34.1
Heavy Atom Count:17
Complexity:352
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes