Dimethylformamide → HCID 58434902, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask under nitrogen, 3,6-di-thiophen-2-yl-1,4-dihydropyrrolo[3,2-b]pyrrole-2,5-dione (Example 2A, 1.8 g, 6 mmol), Cs2CO3 (4.89 g, mmol) and anhydrous DMF (60 mL) were added and stirred at 60° C. 2-Butyloctyl iodide (3.0 mL, 12 mmol) was added in one portion and the reaction mixture was kept at 60° C. for 24 hours. After removing the solvent, chloroform (30 mL) was added and the mixture was stirred for 10 minutes before it was filtered through coarse Celite® diatomaceous earth particles. After concentration, the crude was purified by a short column with a 3:1 mixture of chloroform:hexane as the eluent to give an orange solid (500 mg, yield 13%). 1H NMR (CDCl3, 500 MHz), δ=7.62 (d, J=5.0 Hz, 2H), 7.30 (d, J=3.5 Hz, 2H), 7.13 (dd, J=5.0, 3.5 Hz, 2H), 3.74 (d, J=7.5 Hz, 4H), 1.40-1.00 (m, 38H), 0.87 (t, J=7.5 Hz, 6H), 0.83 (t, J=7.0 Hz, 6H).

Provenance & Evidence