402-07-3, 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 402-07-3 as follows.
To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.
Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem