Potassium Fluoride → 5,5'-Dibromo-4,4'-bis(2-octyldodecyl)-2,2'-bithiophene

Participants

Reaction Conditions

Reaction Steps

2-bromo-3-(2-octyldodecyl)thiophene (5.32 g, 12 mmol), PdCl2(PhCN)2 (46.5 mg, 0.12 mmol), potassium fluoride (1.39 mg, 24 mmol), and dimethyl sulfoxide (DMSO) (60 mL). AgNO3 (4.06 g, 24 mmol) was added to a 100 mL of Schlenk tube, in one portion. The resulting mixture was stirred at 120° C. for 3 h. Additional potassium fluoride (1.39 mg, 24 mmol) and AgNO3 (4.06 g, 24 mmol) were then added to the mixture and the mixture was stirred for 8 h at 120° C. The reaction mixture was then cooled and passed through a Celite pad to remove black solids. The resulting cake was washed repeatedly with ethyl acetate. The filtrate was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, resulting in a crude product. The crude product was purified by silica gel chromatography to produce 2.54 g of the final product, a light yellow oil (48%). 1H NMR (CDCl3, 400 MHz, ppm) δ 6.73 (s, 2H), 2.46-2.44 (d, 4H, J=7.2 Hz), 1.64 (m, 2H), 1.25 (br, 64H), 0.89-0.86 (t, 12H). 13C NMR (CDCl3, 100 MHz, ppm) δ 142.20, 136.03, 124.94, 108.50, 38.51, 34.27, 33.39, 31.93, 31.91, 29.97, 29.67, 29.64, 29.63, 29.59, 29.34, 29.32, 26.53, 22.68, 22.67, 14.08.

Provenance & Evidence