Dimethylformamide → Dibenzo[b,d]furan-3,7-dicarbonitrile

Participants

Reaction Steps

A suspension of 3,7-dibromo-dibenzofuran (18, 10.27 g, 31.51 mmol) and copper(I) cyanide (8.23 g, 94.5 mmol) in DMF (80 mL) was refluxed under N2 for 6 h. The reaction mixture was poured into ice-water (300 mL). The precipitated solid was collected and stirred for 5 h in a solution of ethylenediamine (50 mL) in water (300 mL). The solid was filtered off, washed with water, then stirred in 10% sodium cyanide solution (100 mL) for 4 h. The solid was further purified by suspension in hot ethanol (100 mL) to give a pale yellow powder (6.69 g, 97.43%): mp 322-325° C. (dec.); HPLC method 3 tR=16.56 min (96.6 area %); 1H NMR (300 MHz, DMSO-d6) δ 8.51 (d, J=8.3 Hz, 2 H), 8.48 (s, 2 H), 7.95 (dd, J1=8.3 Hz, J2=1.0 Hz, 2 H); EI-MS m/z 218 (M+). Anal. (C14H6N2.0.23H2O) C, H, N.

Provenance & Evidence