7745-91-7, name is 3-Bromo-4-methylaniline, 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. category: bromides-buliding-blocks
The solution of 4-methoxy-1,3-benzenedichloride (6)(0.93 g, 4.0 mmol) in anhydrous THF (15 mL) was added to3-bromine-4-methylaniline (1.48 g, 8.0 mmol). This solutionwas stirred rapidly at room temperature for about 1 hand then pyridine (1 mL) was added. The solution wasrefluxed for 4-8 h. The residue was recrystallized frommethanol-water to terminal compound 1a (1.81 g, yield85.2%). The other compounds (1b-1i) were prepared with thesimilar method of preparing compound 1a. White solid (The residue was recrystallized by 50%ethanol.); Yield = 85.2%; Rf: 0.38; m.p.: 157.2-158.4 C;IR (KBr) upsilonmax 3340.21, 2971.89, 1665.12, 1601.07,1447.33, 1267.97, 982.92, 758.72 cm-1; 1H-NMR(400 MHz, CDCl3, TMS): delta = 10.06 (s, 2H, 2¡Á -CONH-),8.72 (s, 1H, Ar-2-H), 8.62 (d, J = 6.8 Hz, 1H, Ar-6-H), 8.42(d, J = 7.2 Hz, 1H, Ar-5-H), 8.15 (s, 2H, Ar-2?,2?-H), 7.86(d, J = 4.8 Hz, 2H, Ar-6?, 6?-H), 7.49 (d, J = 7.8 Hz, 2H,Ar-5?, 5?-H), 3.78 (s, 3H, Ar-4-OCH3), 1.43 (s, 6H, Ar-4?,4?-CH3); 13C-NMR (101 MHz, CDCl3): delta = 164.49 (C, C= O), 163.42 (C, C = O), 142.57 (C, Ar-4-C), 141.97 (C,Ar-1?-C), 139.68 (C, Ar-1?-C), 133.63 (C, Ar-1-C), 133.13(C, Ar-3-C), 132.29 (C, Ar-3?-C), 131.26 (C, Ar-3?-C),130.28 (CH, Ar-2-C), 128.92 (CH, Ar-6-C), 127.83 (CH,Ar-5-C), 126.23 (CH, Ar-2?-C), 124.63 (CH, Ar-2?-C),122.65 (CH, Ar-5?-C), 121.31 (CH, Ar-5?-C), 118.91 (CH,Ar-6?-C), 117.79 (CH, Ar-6?-C), 116.46 (C, Ar-4?-C), 115.36 (C, Ar-4?-C), 63.49 (O-CH3, Ar-4-O-CH3), 14.76(2¡Á CH3, Ar-4?,4?-CH3); MS (m/z): 532.9820 [M + H]+.
The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Chen, Guangling; Wang, Chaoqing; Zhang, Zhihao; Liu, Xiujie; Medicinal Chemistry Research; vol. 28; 9; (2019); p. 1413 – 1424;,
Bromide – Wikipedia,
bromide – Wiktionary