2,5-dibromothiophene-3-carboxylic acid,Canonical

3-Thenoic acid (1.49 g, 11.7 mmol) and N-bromosuccinimide (NBS) (4.60 g, 25.8 mmol) were added to degassed DMF (24 mL). The flask was then wrapped with aluminum foil to shield the reaction mixture from light. The mixture was then stirred at 50 °C for 28 h. The mixture was allowed to cool to room temperature, after which it was poured into water (300 mL). The resulting precipitate was collected by filtration and washed with saturated NaCl aq., dried over anhydrous MgSO4, and then filtrated to afford 2, 5-dibromo-3-thenoic acid as a white dasolid in 88percent yield.Compound 1 (2.00 g, 15.6 mmol) was dissolved in glacial acetic acid (25.0 mL) and Br2 (12.4 g, 78.0 mmol) was added to the above solution dropwise at room temperature. The mixture was heated and stirred at 60 °C for 24 h. After the reaction was completed, the mixture was poured into 200 mL of deionized water to quench the reaction. The precipitate was filtered and dissolved in ethyl acetate(EA). The solution in EA was dried with Na2SO4. After evaporation of the solvent, the crude product was purified by recrystallization from EtOH-H2O to give the product as a white powder (3.60 g, yield 80.7percent; 1H NMR (500 MHz, CDCl3; d (ppm)): 13.29 (s, 1H), 7.44(s, 1H)).To a solution of 3-thiophenecarboxylic acid (25.3 g) in acetic acid (200 mL) was added dropwise bromine (21.3 mL), and the mixture was stirred at 50°C for 1 day. A solution of 5-bromo-2-cyano-thiophene-3-carboxylic acid (2.0 g) in dichloromethane (34.97 ml) was treated with oxalyl chloride (1.77 g) and a catalytic amount of N, N-dimethylformamide at roomtemperature. After 1.5 hour, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (35 mL). This solution was slowly added to a solution of cyclopropylamine (815 mg) in tetrahydrofuran (35 mL) under stirring. After 1 hour, the reaction mixture was treated with an aqueous solution of sodium bicarbonate and extracted twice with dichloromethan. The organic phase was dried over sodium sulfate. The crude product was purified by chromatographyover silica gel, eluting with a mixture of ethyl acetate-cyclohexane (2:8). Evaporation of the selected fractions left the title compound as a white powder.1H-NMR (CDCI3, 400 MHz, oe in ppm): 0.58-0.68 (m, 2H), 0.80-0.92 (m, 2H), 2.82-2.91 (m, 1H), 6.5 (brs, 1H), 7.32 (s, 1H).A mixture of compound 2 (2.50 g, 8.74 mmol) and K2CO3 (3.63 g, 9.62 mmol) was dissolved in dimethyl formamide (DMF; 20.0 mL). The mixture was stirred for 1 h under Ar atmosphere and 1-iodo-2-hexyldecane (2.60 g, 9.62 mmol) was added and stirred overnight. Deionized water (50.0 mL) with a small amount of 1M HCl (2-3 mL) was poured into the mixture to quench the reaction, followed by extraction with CH2Cl2. The organic phase was dried with Na2SO4 and the solvent was removed in vacuo. The product was purified by column chromatography on silica gel using hexane/CH2Cl2 (4:1 v/v), yielding the pure compound as a colorless oil (1.70 g, yield 38.0%; 1H NMR (500 MHz, CDCl3; d (ppm)): 7.33 (s, 1H), 4.19-4.18 (d, J 5.8 Hz, 2H), 1.74-1.71 (m, 1H), 1.42-1.27 (m, 14H), 0.89-0.86 (m, 6H)).

Molecular Weight:285.94
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:285.81218
Monoisotopic Mass:283.81423
Topological Polar Surface Area:65.5
Heavy Atom Count:10
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes