10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C12H6Br2O
2,8-Dicyanodibenzofuran 11. A mixture of 2,8-dibromodibenzofuran (10, 10.93 g, 33.53 mmol) and copper(I) cyanide (8.91 g, 102 mmol) in DMF (80 mL) was refluxed under N2 for 9 h. The reaction mixture was poured into ice-water (300 mL). The precipitated solid was filtered off and stirred overnight 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) overnight. The solid was further purified by suspension in hot ethanol (100 mL) to give a white powder (6.97 g, 95.2%): mp 298-300 C. (dec.) (Lit. [37] 299 C.); HPLC method 1 tR=24.07 min (97.3 area %); 1H NMR (400 MHz, DMSO-d6) delta 8.05 (d, J=8.7 Hz, 2 H), 8.12 (dd, J1=8.7 Hz, J2=1.4 Hz, 2 H), 8.85 (d, J=1.4 Hz, 2 H). Anal. (C14H6N2O.0.4H2O) C, H, N. 4,4′-Dibromo-2,2′-dinitrobiphenyl 14 [Moffatt, J. S. 3:6-Diamidinodibenzofuran. J. Chem. Soc. 1951, 625-62]. A suspension of 2,5-dibromonitrobenzene (13, 50.0 g, 178 mmol) and copper powder (100 mesh, 25.0 g, 391 mmol) in DMF (300 mL) was stirred at 137 C. (oil bath) under N2 for 2 h. The mixture was poured into toluene (1000 mL) and stirred for 4 h. Then the mixture was passed through Celite 545. The filtrate was collected and washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was recrystallized from ethanol (650 mL) to give a pale yellow solid (31.33 g, 87.57%): m.p. 143-146 C. (reported 150 C. [Shaw, F. R.; J. Chem. Soc. 1932, 285-297] and 146-148 C. [Yamato, T.; et al., J. Org. Chem. 1991, 56, 6248-6250]); HPLC method 3 tR=18.70 min (97.2%); NMR (300 MHz, CDCl3) delta 8.40 (d, J=2.0 Hz, 2 H), 7.85 (dd, J1=8.2 Hz, J2=2.0 Hz, 2 H), 7.18 (d, J=8.2 Hz, 2 H).
The synthetic route of 10016-52-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; The University of North Carolina at Chapel Hill; US6172104; (2001); B2;,
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