Synthetic Route of 22034-13-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22034-13-5 as follows.
A mixture of (9,9-di-n-hexyl-9H-fluoren-2-yl)boronic acid [J. Am. Chem. Soc, 2004, 126, 13695-13702] (915 mg, 2.42 mmol), 4-bromobenzo[c] [l,2,5]thiadiazole [J. Phys. Chem. B, 2012, 116, 7259-7268] (434 mg, 2.02 mmol), and potassium carbonate (1.20 g, 8.70 mmol) in toluene (20 mL), ethanol (8 mL), and water (12 mL) was placed under vacuum until boiling and backfilled with argon six times. Tetrakis(triphenylphosphine)- palladium(O) (100 mg, 0.087 mmol) was added and the solution heated in an oil bath held at 100¡ãC overnight under a blanket of argon. The solution when then cooled, diluted with water (90 mL), diethyl ether (90 mL), brine (60 mL), and the layers separated. The aqueous solution was extracted with diethyl ether (3 x 60 mL) and the combined organic extracts were washed with water (2 x 60 mL), brine (60 mL), dried over anhydrous magnesium sulphate, filtered on a silica plug, and the solvent removed in vacuo. The crude residue was purified by column chromatography over silica using a dichloromethane: light petroleum mixture (0: 1 to 1 : 10) as eluent to afford AL03-77 as yellow/green oil after removal of the solvent (751 mg, 79percent). 1H NMR (500 MHz, CDC13) delta: 0.66-0.83 (10H, m, HexH), 1.00- 1.12 (12H, m, HexH), 1.95-2.09 (4H, m, HexH), 7.31- 7.40 (3H, m, FIH), 7.71 (1H, dd, = 8.5, 8.5 Hz, BTH), 7.76 (2H, dd, = 1.0, 7.0 Hz, FIH), 7.85 (1H, dd, = 0.5, 8.0 Hz, BTH), .90 (1H, d, = 0.5 Hz, BTH), 7.97 (1H, dd, = 1.5, 8.0 Hz, FIH), 8.00 (1H, dd, = 1.0, 8.5 Hz, FIH). HRMS (ESI-MS) for C31H36N2S [M + Na]+ Calcd: 491.2491 (100percent), 492.2522 (34percent), 493.2511 (10percent). Found: 491.2491 (100percent), 492.2500 (40percent), 493.2480 (12percent).
According to the analysis of related databases, 22034-13-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; BURN, Paul Leslie; SHAW, Paul Edward; (64 pag.)WO2019/79860; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary