1,4-Dibromo-2,5-diiodobenzene → HCID 58340348, compound

Participants

Reaction Conditions

Reaction Steps

A oven dried 2000 cm3 flask is charged with 1,4-dibromo-2,5-diiodobenzene (61.00 g, 125.1 mmol), dichlorobis(triphenylphosphine)palladium(II) (2.195 g, 3.127 mmol) and anhydrous tetrahydrofuran (300 cm3). Once the starting materials are dissolved, a solution of 0.5 M of 3-bromo-2-thienylzinc bromide in tetrahydrofuran (500 cm3, 250.2 mmol) is transfered using a canula and the reaction heated to 85° C. for 3 hours. The reaction is cooled down overnight and the white precipitate filtered off. This precipitate is washed with water (750 cm3) and methanol (250 cm3) to obtain 25.77 g of the title product. Further product is recovered from the initial filtrate. The filtrate is reduced to ca. 90 cm3 in vacuo and then 500 cm3 of methanol is added. The precipitate is filtered off, washed with water (750 cm3) and methanol (250 cm3) and finally triturated three times in hot propan-2-ol to obtain an additional 12.72 g of the title product. (38.49 g, Yield: 55%). NMR (1H, 300 MHz, CDCl3): δ 7.71 (s, 2H); 7.42 (d, J=5.3 Hz, 2H); 7.09 (d, J=5.3 Hz, 2H). NMR (13C, 75 MHz, CDCl3): δ 136.62; 136.10; 135.16; 130.50; 126.97; 123.52; 111.78.

Provenance & Evidence