1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of methyl 2-cyanoacetate (0.89 mL, 10.1 mmol) inDMF (20 mL) at rt was added sodium hydride (0.97 g, 24.2 mmol),and the reaction mixture was stirred at rt for 15 min. Tetrabutylammoniumiodide (0.37 g, 1.0 mmol) and ((2-bromoethoxy)methyl)benzene (3.35 mL, 21.19 mmol) were added, and the reactionmixture was stirred at 90 C for 3 h. Water was added and theaqueous layer was extracted with ether (3). The combinedorganic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was concentrated togive the crude product. The crude product was purified by silicagel chromatography eluting with 0?30percent EtOAc/hexanes to give14 (2.4 g, 65percent yield) as a colorless oil. 1H NMR (500 MHz, CDCl3)d 7.41?7.27 (m, 10H), 4.49 (s, 4H), 3.78?3.69 (m, 5H), 3.45 (s,3H), 2.49?2.40 (m, 2H), 2.06 (dt, J = 14.2, 4.7 Hz, 2H). LC/MS m/z:(M+H)+ calcd for C22H26NO4, 368.19; found 368.3.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-37-9, its application will become more common.
Reference:
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem