1,4-Dibromo-2,5-bis(methylsulfinyl)benzene → 5,5'-(2,5-Bis(methylsulfinyl)-1,4-phenylene)bis(2-propylthiophene)

Participants

Reaction Conditions

Reaction Steps

1,4-dibromo-2,5-bis(methylsulfinyl)benzene 3 (2.60 g, 7.21 mmol) was added to a solution of 2-propyl-5-trimethylstannylthiophene (5.0 g, 17.3 mmol) in anhydrous Toulene (48 mL), and the resulting mixture was purged with nitrogen for 30 min. Pd(PPh3)4 (0.833 g, 0.072 mmol) was then added, and the reaction mixture was heated to 100° C. overnight. Excess Toulene was removed under high vacuum, and the residue was dissolved in ethyl acetate and treated with 10% aqueous KF. The mixture was filtered through a pad of Celite. The filtrate was dried over Mg2SO4, filtered, and the solvent removed in vacuo. The crude product was purified by flash chromatography (silica gel, eluent:hexane/EA) 2:1) to afford 2.63 g (81%) of 2c.

Provenance & Evidence