With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.
5381-20-4, Synthesis of 2-(3-(trifluoromethyl)phenyl)benzo[b]thiophene-3-carbaldehyde (29a): Benzo[b]thiophene-3-carbaldehyde (27) (162 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25 C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), and mixed with 3-iodobenzomethyltrifluoride (354 mg, 1.3 mmol, 1.3 equiv) were then transferred via cannula to the reaction mixture. The resulting mixture was stirred for 1 h at 25 C. The reaction mixture was then quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3¡Á50 mL) and driedanhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:3) furnished compound 29a (281 mg, 92%) as a colourless solid. m.p.: 102.8 – 104.2 C.1H-NMR (400 MHz, CDCl3) delta: 10.02 (s, 1 H), 8.79 (m, 1 H), 7.45-7.87 (m, 7 H).13C-NMR (100 MHz, CDCl3) delta: 185.9, 158.0, 138.0, 136.8, 133.7, 132.4, 131.5 (q, J (C-F)=33.0 Hz), 130.7, 129.5, 127.0 (q, J (C-F)=3.8 Hz), 126.6 (q, J (C-F)=3.8 Hz), 126.5, 126.2, 123.5 (q, J (C-F)=272.5 Hz), 121.7.MS (70 eV, El) m/z (%): 306 (97) [M+], 305 (100), 278 (12), 257 (13), 237 (28), 233 (18), 208 (29), 160 (13), 44 (40).IR (ATR) v (cm-1): 3068, 2866, 2359, 1926, 1745, 1669, 1590, 1520, 1483, 1459, 1438, 1421, 1392, 1351, 1325, 1310, 1288, 1265, 1217, 1178, 1156, 1118, 1097, 1092, 1073, 1051, 1018, 1000, 994, 966, 947, 933, 907, 868, 863, 812, 773, 754, 733, 703, 679, 653, 641, 633, 620, 608, 603.HRMS (El) for C16H9F3OS (306.0326): 306.0326.
5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various fields.
Reference£º
Patent; Knochel, Paul; Mosrin, Marc; US2011/288296; (2011); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem