A three-necked round-bottomed flask was equipped with a stir bar and condenser. Chloroform (25 mL) and acetic acid (25 mL) were added to the reaction flask, then 1,2,4,5-tetra(thiophen-2-yl)benzene (0.830g, 2 mmol, 1 eq.) and N-bromosuccinimide (1.817g, 10 mmol, 5 eq.) were added. The reaction was heated at 75°C for 17 hours in air. Reaction completion was monitored by ¹H NMR of an aliquot every two hours. Upon completion of the reaction, the flask was cooled to room temperature and more chloroform was added until all the solid had dissolved. The organic layer was washed with saturated sodium bisulfite solution (2 x 200 mL) and saturated potassium carbonate solution (2 x 200 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure on a rotary evaporator. The product was recrystallized from 25% ethyl acetate in hexanes to yield a green-brown powder (1.079 g, 1.49 mmol, 75% yield).

¹H NMR (400 MHz, CDCl₃): δ 7.501 (s, 2H), 6.964 (d, 4H, J = 3.6 Hz), 6.744 (d, 4H, J = 3.6 Hz) 

¹³C NMR (400MHz, CDCl3): δ 141.607, 133.408, 133.264, 127.426, 127.047, 126.361.

Mass Spec: Calculated: 722.1780 g/mol; observed: 722.6476 g/mol.