2-Bromoanthracene

Yellow solid

In a preferred embodiment, To a 500 mL three-necked flask was added 275.0 g diglyme, 68.0 g (0.51 mol) of aluminum chloride solid was added slowly, The control temperature was 60 ° C, About 20min feeding is completed, The system becomes gray or milky white turbidity.Cooling to 30 , stand-by.A further 1 L three-necked flask was charged with 49.2 g (0.17 mol) of 2-bromoanthraquinone, 200.0 g diglyme, Stir, 27.5 g (0.51 mol) of potassium borohydride was added, The system becomes yellow-green turbidity, Heating up to 105 ° C, And heat for 30 minutes, During the heating process, the system changed from yellow-green turbidity to pink turbidity, Finally into brown turbidity.Insulation is completed, The above-mentioned aluminum chloride solution was slowly added to the system, Control the internal temperature between 90 ~ 110 , Drop before the first 1/3 of the exothermic reaction, After 2/3 of the process, the endothermic reaction, Dripping with the full range of bubbles, System from brown turbidity into bright yellow turbidity, Finally turned into yellow turbidity.The feeding process is about 20 minutes.Feeding is completed, Quickly cool the water bath to 40 ° C.The system was poured into concentrated hydrochloric acid / water / ethanol (100 g / 400 g / 300 g)System exotherm, accompanied by a large amount of gas generated.Hydrolysis process control system temperature below 60 .Hydrolysis is completed, cooling to 25 , Filter, 100.0g of water and 100.0g of anhydrous ethanol were leaching filter cake was yellow filter cake, This product is crude product.According to crude:Anhydrous ethanol = 1: 10 by the addition of absolute ethanol, Heating up to 50 ~ 60 , Stirring for 1.0 hr, Cooling to 25 ~ 30 , Insulation 0.5hr, suction filter, A small amount of anhydrous ethanol leaching filter cake was white solid, This is the product quality, Dried (50 ° C, 200 Pa, 5 hr) to give 35.8 g of a white powdery solid, This is the product quality, the yield of 82.02percentCompound 1 (2 g, 6.9 mmol), hydroiodic acid (10.6 mL), and hypophosphorous acid (6.4 mL) were dissolved in acetic acid (17 mL). The mixture was stirred for 96 h at 150 °C. The reaction mixture was cooled to room temperature. The precipitate was filtered and washed with ethanol. The solid was purified via soxhlet extraction with toluene, yielding compound 2 as a pure yellow solid. Yield: 1.1 g (61percent). A 1-L, 3-necked flask was fitted with a distillation head and purged with N2. The system was charged with 2-bromoanthraquinone (29.0 g, 101 mmol), cyclohexanol (350 mL), and aluminum tri-sec-butoxide (140 mL, 550 mmol). The mixture was heated and became deep amber as distillate was collected until the pot temperature was 162 °C. The reaction was heated at 160 °C for 16 h and then cooled to room temperature. The mixture was mixed with tetrahydrofuran (100 mL) and poured onto a 2 L filter frit to isolate the black solid. The solid was stirred on the frit with 6 M HCl (100mL) and then further washed with water (500 mL). The gray crude product was air-dried overnight. The solid was purified further by gradient sublimation at a source temperature of 120°C to afford 12.6 g (48percent) of off-white product. DSC data: peak temp 220 °C (ΔH = 126 Jg2-Bromoanthraquinone 10 (8.50 g, 0.0296 mol, 1 equiv) and a 50:50 mixture of isopropyl alcohol and tetrahydrofuran (200 mL) were stirred for 10 minutes at 0° C. forming a yellow suspension. NaBHEXAMPLES

Molecular Weight:257.12
XLogP3:5.5
Exact Mass:255.98876
Monoisotopic Mass:255.98876
Heavy Atom Count:15
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes