78% |
With tetrakis(triphenylphosphine) palladium(0); Aliquat (at)366; potassium carbonate; In tetrahydrofuran; water; toluene; at 80℃;Inert atmosphere; |
To a solution of 2-bromo-5-(2-octyldodecyl)thiophene (5) (1.02 g, 2.25 mmol),<strong>[171364-83-3]4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene</strong> (0.500 g, 2.01 mmol), and K2CO3 (0.830 g, 6.01 mmol) intoluene/THF/water (7 mL, 4/2/1, v/v/v) was added tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.0121 mmol) and aliquat 336 (4 drops), and then the solution was heated at 80 C for overnight under an argon atmosphere. After quenching the reaction with water, the product was extracted with toluene. The toluene solution was then washed with brine. After drying the toluene solution over MgSO4 followed by filtration, the filtrate was concentrated under thereduced pressure. The crude product was purified by silica gel column chromatography using hexane, then CH2Cl2 as eluents to afford 6 as orange oil (0.849 g, 78%). 1H NMR(300 MHz, CDCl3, delta, ppm, 25 C): 8.21 (d, J=9.0 Hz, 2H,aromatic proton), 7.67 (d, J=9.0 Hz, 2H, aromatic proton), 7.31 (d, J=3.6 Hz, 1H, aromatic proton), 6.79(d, J=3.9 Hz,1H, aromatic proton), 2.78 (d, J=6.6 Hz, 2H, thiophene-CH2-), 1.73-1.60 (m, 1H, thiophene-CH2-CH), 1.39-1.17(m, 32H, -CH2-), 0.88 (t, J=6.0 Hz, 6H, -CH3). 13C NMR (75 MHz, CDCl3, delta, ppm, 25 C): 148.04, 146.26, 141.09,139.11, 127.05, 125.66, 125.44, 124.51, 40.14, 34.88, 33.30-26.72 (14 carbons), 22.83 (2 carbons), 14.27 (2 carbons).IR (NaCl), v (cm-1): 2925 (alkyl C-H), 1594, 1338 (N-O stretching). MS (MALDI-TOF) m/z [M+H+]: Calcd forC30H47NO2S, 485.33; found, 486.44. Anal. Calcd for C30H47NO2S: C, 74.18; H, 9.75; N, 2.88. Found: C, 74.30; H,10.19; N, 2.92. |