2,6-Dibromodithieno[3,2-b:2',3'-d]thiophene

White to yellow to tan solid

Synthesis of Compound 2N-bromosuccinimide (5.87 g, 33 mmol) was gradually added to a solution of the compound 1 (by Aldrich, 2.94 g, 15 mmol) in dewatered DMF (60 mL) at 0° C. The mixture was heated up to room temperature, stirred overnight, and then poured into water, and the formed precipitate was taken out. This was washed with methanol and recrystallized in chloroform/methanol to give an off-white crystal of the compound 2 (yield: 5.14 g, 97percent).To the flask was added compound 1 (2.94 g, 15.0 mmol), Dry DMF (60 ml), Cooled to 0 ° C, To this was slowly added bromosuccinimide (5.87 g, 33.0 mmol).After completion of the addition, the mixture was warmed to room temperature and stirred overnight. The reaction solution was poured into water to give a precipitate, which was filtered and washed with methanol. The product was recrystallized from a chloroform / methanol mixed solvent and dried in vacuo to give an off-white solid (5.14 g, 97percent yield).22.0 g (0.112 mol) of the compound represented by the formula 3-e obtained in the above reaction scheme 19 and 440 mL of N, N-dimethylformamide were added to a 1 L round bottom flask, and then 43.9 g (0.247 mol) of N-bromosuccinimide, Was slowly added and stirred for 30 minutes. 1 L of water was poured and the resulting solid was filtered and dried to obtain 37.0 g (93.2percent) of the compound represented by the formula 3-f.Dithieno[3, 2-b:2′, 3′-d]thiophene (0.98 g, 5.0 mmol) in chloroform (20 mL) was reacted with N-bromosuccinimide (NBS, 2.0 g, 11.2 mmol) at room temperature overnight. Batch-wise addition of NBS is necessary. The light yellow suspension was treated with water and filtered off. After silica column chromatography with petroleum ether, pale needle crystals were obtained (1.8 g, 90percent yield). Synthesis of Compound 2N-bromosuccinimide (5.87 g, 33 mmol) was gradually added to a solution of the compound 1 (by Aldrich, 2.94 g, 15 mmol) in dewatered DMF (60 mL) at 0 C. The mixture was heated up to room temperature, stirred overnight, and then poured into water, and the formed precipitate was taken out. This was washed with methanol and recrystallized in chloroform/methanol to give an off-white crystal of the compound 2 (yield: 5.14 g, 97%).1H NMR (500 MHz, CDCl3): delta 7.28 (s, 2H).To the flask was added compound 1 (2.94 g, 15.0 mmol), Dry DMF (60 ml), Cooled to 0 C, To this was slowly added bromosuccinimide (5.87 g, 33.0 mmol).After completion of the addition, the mixture was warmed to room temperature and stirred overnight. The reaction solution was poured into water to give a precipitate, which was filtered and washed with methanol. The product was recrystallized from a chloroform / methanol mixed solvent and dried in vacuo to give an off-white solid (5.14 g, 97% yield).22.0 g (0.112 mol) of the compound represented by the formula 3-e obtained in the above reaction scheme 19 and 440 mL of N, N-dimethylformamide were added to a 1 L round bottom flask, and then 43.9 g (0.247 mol) of N-bromosuccinimide, Was slowly added and stirred for 30 minutes. 1 L of water was poured and the resulting solid was filtered and dried to obtain 37.0 g (93.2%) of the compound represented by the formula 3-f.Dithieno[3, 2-b:2?, 3?-d]thiophene (0.98 g, 5.0 mmol) in chloroform (20 mL) was reacted with N-bromosuccinimide (NBS, 2.0 g, 11.2 mmol) at room temperature overnight. Batch-wise addition of NBS is necessary. The light yellow suspension was treated with water and filtered off. After silica column chromatography with petroleum ether, pale needle crystals were obtained (1.8 g, 90% yield). 1H NMR (400 MHz, CD2Cl2, ppm) delta: 7.27 (s, 2H). 13C NMR (100 MHz, CDCl3, ppm) delta: 112.32, 123.17, 130.82, 139.05. EI-MS m/z (M+): Calcd. for C8H2Br2S3, 352; found, 352.1)

Molecular Weight:354.1
XLogP3:5.9
Hydrogen Bond Acceptor Count:3
Exact Mass:353.76649
Monoisotopic Mass:351.76854
Topological Polar Surface Area:84.7
Heavy Atom Count:13
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes