2,8-Dibromodibenzothiophene

White to light yellow solid

To a slurry of dibenzothiophene (15.0 g; 0.0814 mol) in chloroform (80 ml) was slowly added bromine (10.5 ml; 32.6 g; 0.18 mol) in chloroform (20 ml). The red- brown reaction mixture was stirred at room temperature for 24 h and then solvent removed by distillation at atmospheric pressure. The residue was washed three times with methanol until the filtrate became almost colourless. The off-white solid was dried under vacuum at 75 °C. Yield 20.5 g (74 percent). The product was sublimed to give an analytically pure colourless solid, 18.2 g (89 percent). M.p 223°C (DSC, onset) and 227°C (DSC, peak) [ Lit., 226 °C, TCI]In step three 150mL flask 1) to give crystals of dibenzothiophene (5.0g, 0.027m 1) was dissolved in 30mLChloroform. Liquid bromine was added dropwise at ° C, square (3. lmL, 0.06lmo 1), overnight at room temperature under a nitrogen atmosphere, the crude product was filtered and washed with methanol to give a white powder, yield 85percent. 1 NMR, GC-MS analysis showed that the resultant was a target productTo a mixture of dibenzo[b, d]thiophene (Example 1-1) (4g, 21.73 mmol) and CH2CI2 (100 mL) was added bromine (3.35 ml, 65.22 mmol) at 0°C under nitrogen atmosphere. The reaction mixture was stirred at room temperature overnight. The organic layer was collected and concentrated in vacuo to yield a solid product. The product obtained was recrystallized using CH2CI2 to afford the title compound (Example 1-2) as a white solid (6.34 g, 85.33 percent). 1H NMR (500 MHz, ODd3) O 8.22 (d, J= 2 Hz, 2H), 7.70 (d, J= 8.5 Hz, 2H), 7.57 (dd, J=8.5, 2Hz, 2H).Under a argon atmosphere, sulfurfluorene (20 g, 108.54 mmol) was added to a 250 ml two-necked flask, And then added 100 ml of chloroform for complete dissolution, Add 0.5g iodine elemental, in the case of dark, A solution of bromine (38.16 g, 238.80 mmol)The reaction solution was stirred at 0 ° C under ice-cooling for 2 hours, Followed by stirring at room temperature for 2 hours, Adding saturated sodium bisulfite to quench the liquid bromide, pour the reaction mixture into water, Extracted with ethyl acetate, and the organic layer was completely washed with brine, Dried over anhydrous magnesium sulfate; the solution was concentrated to give the crude product as a white solid which was recrystallized from chloroform to 85percent yield.Under an argon atmosphere, Sulfur fluorene (20 g, 108.54 mmol) was added to a 250 ml two-necked flask followed by 100 ml of chlorineComplete imitation of the dissolution, adding 0.5g of iodine simple substance, in the dark, the dropwise addition of liquid bromine (38.16g, 238.80mmol), the reaction solution was stirred at 0 ° C for 2 hours in an ice bath and then at room temperature for 2 hours The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed thoroughly with brine and then dried over anhydrous magnesium sulfate. The solution was concentrated to give a crude white solid which was recrystallized from chloroform with a yield of 85percentDibenzothiophene (15.1552 g, 82.25 mmol) was dissolved in CHCl3 (150 mL), and Br2 (13.0 mL, 253.72 mmol) was gradually added to the mixture at 0° C. After 2 hours, the temperature of the reaction mixture was raised to room temperature, and stirred for 3 days. An excessive amount of MeOH was added to the mixture, and the mixture was stirred for 30 minutes, filtered in vacuum, and washed with an excessive amount of methanol, thereby white product 8, i.e., 2, 8-dibromodibenzothiophene (22.87 g, 66.86 mmol, 81percent).Dibenzo [b, d] thiophene (10 g, 54.3 mmol, 1.0 eq) was dissolved in 30 ml of dimethylformamide, And slowly added to the flask at 25 . After reacting for 5 hours, it was precipitated with 200 ml of distilled water, followed by filtering and drying to obtain 12.5 g of the target compound. (Yield: 67.5percent)To a solution of dibenzothiophene (9.2 g, 50.0 mmol) in chloroform (100 mL), bromine (7.7 mL, 150 mmol) was dropwise added at 0 °C by stirring. Under nitrogen atmosphere the reaction mixture was stirred and kept overnight at room temperature. Saturated NaHSO3 aqueous solution was added to the mixture. Then, the crude product was filtered off and washed with methanol to isolate 2, 8-dibromodibenzothiophene(3). The product was obtained as a white powder in 67percent yield. 1H NMR(400 MHz, CDCl3, TMS) δppm: 8.22 (s, 2H), 7.71–7.69 (d, J=8.4 Hz, 2H), 7.58–7.56 (dd, J=10.4 Hz, 2H).2L reaction flask to dissolve the benzothiophene 100g (0.543mol) in 800mL of dichloromethane. Then slowly addeddropwise at room temperature, bromine 69.5mL (1.357mol) to the reaction solution in 200mL dichloromethane. After stirring for an 12 hour the reaction solution was poured into a saturated sodium sulfite aqueous solution and extractedwith dichloromethane. After separation the organic layer was washed with saturated brine. The filtered organic layer wasdried over anhydrous magnesium sulfate. The filtrate was evaporated under reduced pressure and then recrystallized withdichloromethane and methanol was prepared an intermediate compound of the offwhite[99-1]105g (57percent).Into a mixture of dibenzothiophene (50.0 g, 272 mmol), Fe(1.00 g, 18.0 mmol) and CHCl3 (400 mL) was added Br2 (35.0 mL, 680 mmol) (diluted with CHCl3 (100 mL)) slowly at 0 C. The mixture was gradually warmed to room temperature with vigorously stirring overnight. Then aqueous solution of NaHSO3 (28.3 g, 272 mmol) was added to quench the reaction. The mixture wasfiltered, and the residue was washed with water and purified byrecrystallization from THF to afford 1 as a white crystal (39.0 g, 41.9percent). 1H NMR (300 MHz, CDCl3) d (ppm): 8.23 (d, J 1.8 Hz, 2H), 7.72e7.69 (d, J 8.4 Hz, 2H), 7.59e7.56 (dd, J 8.4 Hz, J 2.0 Hz, 2H). 13C NMR (75 MHz, CDCl3) d (ppm): 138.75, 136.30, 130.43, 124.86, 124.33, 118.76. MS (APCI) calculated for C12H6Br2S: 342.1, found: 343.0. Elemental analysis calculated for C12H6Br2S: C, 42.14;H, 1.77; S, 9.37, found: C, 41.62; H, 1.99; S, 9.86.

Molecular Weight:342.05
XLogP3:5.7
Hydrogen Bond Acceptor Count:1
Exact Mass:341.85365
Monoisotopic Mass:339.85570
Topological Polar Surface Area:28.2
Heavy Atom Count:15
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes