2,8-DIBROMODIBENZOFURAN

To a mixture of dibenzo(b, d)furan (4g, 23.8 mmol) and CH2CI2 (100 ml), was added bromine (3.66 ml, 71 .4 mmol) at 0°C under nitrogen atmosphere. The reactionmixture was stirred at room temperature overnight. The organic layer was collectedand concentrated in vacuo to yield a solid product. The product obtained wasrecrystallized using CH2CI2 to afford compound (Example 14-1)asawhite solid (5.85g, 75.7percent)(10 g, 59 mmol, 1.0 eq) was dissolved in 30 ml of dimethylformamide and slowly added at 25 ° C to a flask in which 30 ml of dibenzo [b, d] furan was dissolved in 30 ml of dimethylformamide, followed by addition of n-bromosuccinimide (21.69 g, 121 mmol, 2.05 eq) do.After 5 hours of reaction, the reaction mixture was precipitated with 200 ml of distilled water, filtered and dried to obtain 14.55 g of the title compound (yield: 75.07percent).(1) Synthesis of Compound (291-a) [0252] [0253] Into a three-necked flask, 168.1 g (1000 mmol) of dibenzofuran and 1600 ml of dichloromethane were charged, and the reaction vessel was cooled to 0 °C in a nitrogen atmosphere. After adding 125 ml of a dichloromethane solution of 255.8 g of bromine dropwise into the reaction vessel over 40 min, the contents were stirred at room temperature for 12 h. After the reaction, the reaction vessel was cooled to 0 °C and then 500 ml of water and 100 ml of a 20percent aqueous solution of NaHSO(1) Synthesis of compound (140-a) [0243] [0244] In a three-neck flask, 168.1g (1000 mmol) of dibenzofuran and 1600 ml of dichloromethane were placed. The reactor was cooled to 0°C in a nitrogen atmosphere. To the reactor, 125 mL of a dichloromethane solution of 255.8g of bromine was added dropwise over 40 minutes, and the resultant was stirred at room temperature for 12 hours. [0245] After completion of the reaction, the reactor was cooled to 0°C. 500 mL of water was added, and further, 100 ml of a 20percent aqueous NaHSOIn a 500 mL three-neck flask were put 8.4 g (50 mmol) of dibenzofuran and 100 mL of carbon tetrachloride. A solution prepared by dissolving 17 g (110 mmol) of bromine in 50 mL of chloroform was dripped through a dropping funnel into the three-neck flask over about 20 minutes. Then, this solution was stirred at room temperature for 7 days. After that, this solution was washed with a saturated solution of sodium hydrogen carbonate, an aqueous solution of sodium thiosulfate and saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity filtered. The resulting filtrate was concentrated, and the obtained solid was recrystallized from chloroform. Accordingly, 6.4 g of a white powder was obtained in 40 percent yield, which was the substance to be produced.1a) (1)

Molecular Weight:325.98
XLogP3:5.8
Hydrogen Bond Acceptor Count:1
Exact Mass:325.87649
Monoisotopic Mass:323.87854
Topological Polar Surface Area:13.1
Heavy Atom Count:15
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes