1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

5-(2-ethylhexyl)-4, H-thieno[3, 4-c]pyrrole-4, 6(5H)-dione (0.27 g, 1.01 mmol) was dissolved in concentratedsulfuric acid (1.6 mL) and trifluoroacetic acid (3.4 mL). NBS (0.543 g, 3.05 mmol) was added in one portion and the reaction mixturewasstirred at room temperature overnight. The resultant solution wasthen diluted with water (100 mL) and extracted with dichloromethane.The organic phase was washed with KOH solution, further dried over anhydrous magnesium sulfate and evaporated toafford the crude product as orange crystals. Purification by columnchromatography using silica gel and hexane/chloroform (3:2) gave1, 3-dibromo-5-(2-ethylhexyl)-4H-thieno[3, 4-c]pyrrole-4, 6(5H)-dione (0.34 g, 79percent) as pink solid. 1H NMR (400 MHz, CDCl3): δ 3.49(d, J 7.3 Hz, 2H), 1.81-1.76 (m, 1H), 1.35-1.27 (m, 8H), 0.93-0.88(t, 6H). 13C (100 MHz, CDCl3): δ 160.46, 134.46, 112.65, 42.26, 37.80, 30.13, 28.13, 23.43, 22.54, 13.66, 9.95. Mp: 110.5-112 °C. MALDITOF:calculated for C14H17Br2NO2S [M+H]+ 424.5344.Compound 1 (1.40 g, 5.28 mmol) was dissolved in sulfuric acid (7.8 mL) and trifluoroaceticacid (26 mL). While stirring, NBS (2.81 g, 15.8 mmol) was added and the reaction mixturewas stirred at roomtemperature overnight. The mixture was poured into water and extractedwith dichloromethane. The organic phases were combined, washed with brine, and driedwithmagnesiumsulfate. The product was obtained by column chromatography using chloroform:hexane (2:1). Yield: 1.70 g (76.2percent). 1H NMR (400 MHz, CDCl3): δ (ppm) 3.60 (d, 2H), 1.37 (m, 9H), 0.90 (m, 6H).To a solution of the 5-(2-ethylhexyl)thieno[3, 4-c]pyrrole-4, 6-dione (0.50 g, 1.88 mmol) in trifluoroacetic acid (5 mL) and conc.H2SO4 (2 mL) was added NBS (1.10 g, 6.18 mmol) in portions. Themixture was stirred at room temperature overnight. Then, waterwas added and the mixture was extracted with dichloromethanetwice. The organic phase was dried over Na2SO4. After removingsolvent under vacuum, the crude product was purified by silicacolumn to give the title compound as white powder with 75percent yield.Mp: 104 °C. FTIR (KBr) v/cm-1 2956, 2929, 1697, 1535, 1388, 1054, 958, 746, 680. 1H NMR (CDCl3, ppm): 3.52 (d, J 7.14 Hz, 2H), 1.81e1.77 (m, 1H), 1.38-1.29 (m, 8H), 0.94-0.92 (m, 6H). 13C NMR(CDCl3, ppm): 160.87, 134.90, 113.13, 42.81, 38.36, 30.69, 28.72, 24.00, 23.13, 14.26, 10.55. HRMS (ESI) (M+, C14H17Br2NO2S): calcd, 420.9347; found, 420.9341.2 mmol of 3, 4-thiophenedicarboxylic anhydride and 3mmol 2-ethyl-1-hexylamine was added to a refluxing reactor equipped with a stirrer, 15 mL of a toluene solvent was added, The reaction was refluxed for 20 h at 130 °C under nitrogen and the reaction was allowed to cool to room temperature. And 16 mmol of dibromo sulfoxide was added with stirring at 0 °C, Then, 18 mmol of anhydrous pyridine was added thereto, and the mixture was stirred at room temperature for 3 hours. Heated to 130 °C reflux reaction 20h, the end of the reaction, the reaction cooled to room temperature, And then the product slowly dumped in a beaker containing ice, stirring constantly, The organic layer was collected by extraction with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate, filtered, evaporated, and subjected to column chromatography, rotary distillation, suction filtration and vacuum drying to obtain a compound of the formula of the product, the product yield was 90percent.

suzuki reaction

Molecular Weight:423.2
XLogP3:5.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:422.93263
Monoisotopic Mass:420.93468
Topological Polar Surface Area:65.6
Heavy Atom Count:20
Complexity:367
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes