Toluene, anhydrous, 99.8% Aldrich
1,2,4,5-tetrabromobenzene, 97% Aldrich
2-(tributylstannyl)thiophene, 97% Aldrich
tetrakis(triphenylphosphine)Palladium(0), 99% Aldrich

A three-necked round-bottomed flask was equipped with a condenser, three septa, and a stir bar. The flask was purged with nitrogen gas for 30 minutes. Anhydrous toluene (75 mL) was added under nitrogen. 1,2,4,5-Tetrabromo benzene (2.5 g, 6.35 mmol, 1 eq.) and 2-(tributylstannyl)thiophene (10 mL, 31.75 mmol, 5 eq.) were added. A catalytic amount (spatula tip) of tetrakis(triphenyl phosphine)palladium(0) was added and the reaction was allowed to reflux at 120°C for 16 hours. Completion of the reaction was monitored through TLC (10% ethyl acetate/hexanes, product R_f = 0.51). The reaction was taken off heat and the slushy was dissolved completely in ethyl acetate. The organic layer was washed two times with 10% sodium hydroxide solution ( 200 mL) to remove tin and then dried over sodium sulfate, filtered, and concentrated under reduced pressure on a rotary evaporator to yield the crude product. The material was directly recrystallized from 25% ethyl acetate in hexanes to give grey-tan product (2.28 g, 5.61 mmol, 88%).

¹H NMR (400 MHz, CDCl₃): δ 7.664 (s, 2H), 7.303 (m, 4H), 6.974 (m, 8H).
¹³C NMR (400 MHz, CDCl₃): δ 141.764, 133.565, 133.421, 127.583, 127.204, 126.518.
Mass Spec: Calculated 406.5940 g/mol; Observed 407.0079 g/mol

Chem. Mater., 2008, 20 (7), pp 2484–2494.