3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Compound 3 (1.01 g, 2.05 mmol) was charged in a 100 mLsingle-neck round–bottom flask filled with 50 mL of CHCl3.The mixture was cooled to 273 K and stirred while Nbromosuccinimide(NBS) was added in small portions. Themixture was allowed to warm to room temperature and stirredfor 2 h following complete addition of NBS. The reactionmixture was poured in water and extracted with CHCl3.Then CHCl3 was evaporated, the resulting red solid (darkred) was purified by column chromatography using CHCl3/petroleum ether as eluent. 0.95 g of 4 [31] were isolated (71percentyield). 1H NMR (500 MHz, CDCl3): (ppm) = 8.30 (d, J = 3.7 Hz, 2 H), 6.62 (d, J = 3.7 Hz, 2 H), 3.99 (add, J = 2.7 Hz, 7.4 Hz, 4 H), 1.78–1.68 (m, 2 H), 1.39–1.24 (m, 16 H), 0.92 (t, J = 7.5 Hz, 6 H), 0.88 (t, J = 7.0 Hz, 6 H). 13C(75 MHz, CDCl3): (ppm) = 161.1, 146.4, 132.9, 126.4, 122.4, 115.7, 106.4, 46.4, 40.2, 30.7, 28.9, 23.9, 23.3, 14.2, 10.8. FTIR(KBr) ν max = 3422, 3084, 2957, 2926, 2859, 1657, 1556, 1504.9, 1450, 1406, 1308, 1261, 1233, 1165, 1100, 1072, 1027, 967, 833, 810, 731, 709, 635, 466, 430 cm−Charge a 500-ml eggplant-shape flask with the above- prepared compound (b) (3.0 g, 5.7 mmol), N-bromosuccinimide (2.5 g, 13.8 mmol), and chloroform (200 ml). Agitate the flask content for 12 hours at 0° C. under light shielding condition. After distilling the solvent away under reducedpressures, add MeOR (100 ml) to the flask. Separate the precipitate by filtration. Thus, a dark green powder (4.8 g, 71.0percent) is obtained. mlz=683.1 (M+H)3.56 g of 2, 5-diethylhexyl-3, 6-dithiophen-2-ylpyrrolo[3, 4-c]pyrrolo-1, 4-dione dissolved in 150 ml chloroform (CF) was added to a 500 ml two-necked flask. 2.50 g of N-bromosuccinimide (NBS) was added, a small amount of acetic acid was added, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed by confirming thin-layer chromatography (TLC), the solvent was concentrated to about 20 ml under reduced pressure, and ethanol was added and a solid precipitate was filtered through a filter. The solid thus separated was again dissolved in chloroform, and short column was carried out using silica to obtain a black powder. (Yield: 70percent).the formula (5) Compound 6 (2.00g, 3.81mmol) was dissolved in 50ml of tetrahydrofuran (THF), cooled to 0 ° C, then added in three portions N- bromosuccinimide (NBS ) (1. 42g, 8. OOmmol), while dropping a few drops of glacial acetic acid. After 12 hours under reduced pressure the reaction solvent was distilled off, boiling range 60 ° C -90 ° C petroleum ether as eluent over a silica gel column to give 1. 69g of the formula (5) Compound 7 in a yield of 65percent.Cmpd 1 (857.1 mg, 1.633 mmol) was solubilized in 60 mL CHCl3 previously deacidified onbasic alumina. The solution was stirred in the dark, degassed and an argon flow wasmaintained during the entire reaction. NBS (467.5 mg, 2.627 mmol, 1.6 equiv) was added inone portion. The reaction medium was evaporated, taken up in CH2Cl2, washed with water and brine, driedover Na2SO4. Bis- and mono-brominated products were separated by repetitive chromatography columns onsilica gel using at first a gradient of toluene/petroleum ether (50/50 to 100/0) as eluent, then a gradient ofCH2Cl2/petroleum ether (70/30 to 100/0). The bis-brominated product (3) was obtained as a deep purplesolid (73percent, 815.1 mg) and the mono brominated (2) as a fushia-purple solid (107.0 mg, 11percent).NBS (230.5 mg, 1.295 mmol, 1.2 equiv) was added to a degassed solution of cmpd 1 (555.0mg, 1.058 mmol) in deacidified CHCl3. The reaction medium was stirred in the dark underan argon flow at rt for 30 min. The solution was evaporated and the residue was taken up inCH2Cl2, washed with water, brine and dried over Na2SO4. Purification on silica gel column chromatographyusing a gradient of CH2Cl2/toluene/petroleum ether (5/55/40, 13/50/37, 100/0/0) afforded the monobrominatedcmpd (2) in 53percent as a fushia-purple solid. The bis-brominated product (3) was also isolated in26 percent as a dark purple solid and 19 percent of the starting material was recovered.

suzuki reaction

Molecular Weight:682.6
XLogP3:9.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:14
Exact Mass:682.07210
Monoisotopic Mass:680.07415
Topological Polar Surface Area:97.1
Heavy Atom Count:38
Complexity:865
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes