360576-01-8 Methyl 6-bromobenzo[b]thiophene-2-carboxylate 22474078, abenzothiophene compound, is more and more widely used in various fields.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.360576-01-8,Methyl 6-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.
Ester 9 (6.8 g, 25.0 mmol) was dissolved in THF (anhydrous, 50 mL) and cooled to 0 oC. Lithium dimethylammonium borohydride3 (50 mL, 50.0 mmol, 1.0 M THF/hexane) was added drop-wise. After 5 min of stirring, the reaction was complete as judged by TLC and was quenched with HCl (3.0 M) under vigorous stirring until the evolution of gas ceased. The organic layer was separated, and the aqueous layer extracted with EtOAc (3x). The combined organic layers were washed with water and brine followed by drying (Na2SO4). Evaporation of solvent gave a yellow solid, which was recrystallized from isopropanol/water to give the desired primary alcohol as white crystals. (5.7 g, 94% yield), mp 111-113 oC. IR (thin film, cm-1) 3203, 3071, 2901, 2853, 1577, 1523, 1444, 849, 841; 1H NMR (CDCl3) delta 7.95 (d, J = 1.5 Hz, 1H), 7.57 (d, J = 8.5 Hz, 1H), 7.44 (dd, J = 1.5, 8.5 Hz, 1H), 7.17 (d, J = 1.0 Hz, 1H), 4.91 (s, 2H), 1.97 (br s, 1H); 13C NMR (CDCl3) delta 145.8, 141.6, 138.5, 128.0, 125.1, 124.8, 121.1, 118.3, 60.9; HRMS (EI) for C9H7BrOS [M]+ calcd, 241.9401, found, 241.9404 (error = 1.2 ppm)., 360576-01-8
360576-01-8 Methyl 6-bromobenzo[b]thiophene-2-carboxylate 22474078, abenzothiophene compound, is more and more widely used in various fields.
Reference£º
Article; Zuckerman, Nathaniel B.; Kang, Xiongwu; Chen, Shaowei; Konopelski, Joseph P.; Tetrahedron Letters; vol. 54; 11; (2013); p. 1482 – 1485;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem