Chlorotrimethylsilane → HCID 58340351, compound

Participants

Reaction Conditions

Reaction Steps

A oven dried 1000 cm3 three neck flask is charged with 2,2′-(2,5-dibromobenzene-1,4-diyl)bis(3-bromothiophene) (12.00 g, 21.51 mmol) and anhydrous THF (430 cm3). The reaction is cooled down to −78° C. using a acetone dry ice bath, and then a 2.0M solution (22.0 cm3, 44.1 mmol) of lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene is added dropwise. After the addition completion, the reaction mixture is kept at 78° C. for a hour, and then chlorotrimethylsilane (6.00 cm3, 47.3 mmol) is added quickly. The reaction is allowed to reach 23° C. overnight, and then methanol (100 cm3) and water (400 cm3) is added. The mixture is extracted with diethyl ether (3×300 cm3). The combined organic phases are washed with diluted aqueous chlorhydric acid (3×250 cm3) and water (300 cm3), dried over magnesium sulfate, and then the solvent removed in vacuo. The crude product is recrystallized in propan-2-ol to obtain the title product. (11.12 g, Yield: 74%). NMR (1H, 300 MHz, CDCl3): δ 7.68 (s, 2H); 7.16 (s, 2H); 0.36 (s, 18H). NMR (13C, 75 MHz, CDCl3): δ 142.52; 139.96; 136.60; 136.39; 136.25; 123.11; 112.71, −0.16.

Provenance & Evidence