These common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, its 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. Safety of ((2-Bromoethoxy)methyl)benzene
506 mg (60percent in oil, 13 mmol equivalents) of sodium hydride was added to 5.0 mL of tetrahydrofuran, and the mixture was cooled to about 0°C in an ice bath. 3.2 mL (20.7 mmol equivalents) of diethyl malonate was added thereto (solution A). 2.3 g (10.7 mmol equivalents) of 2-benzyloxy-1-bromoethane was dissolved in 3.0 mL of tetrahydrofuran, this was added dropwise to solution A over 10 minutes, and the mixture was refluxed while heating overnight. After completion of the reaction, a 0.5 mol/L aqueous solution of hydrochloric acid was added dropwise to the reaction liquid, and the mixture was extracted three times with diethyl ether. The combined diethyl ether layers were washed with brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v) = 20/1) to give 2.85 g (9.67 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)malonate. [0115] 1H-NMR (solvent: deuterated chloroform) of diethyl 2-(2-benzyloxyethyl)malonate: delta 7.36-7.28 (m, 5H), 4.48 (s, 2H), 4.21-4.14 (m, 4H), 3.60 (d, J = 7.3 Hz, 1H), 3.53 (t, J = 5.5 Hz, 2H), 2.22 (dt, J = 5.5, 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 6H)
The synthetic route of ((2-Bromoethoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Nihon Medi-Physics Co., Ltd.; National University Corporation Hokkaido University; NAKATA, Norihito; OKUMURA, Yuki; KIRIU, Masato; NAGATA, Eriko; MATSUMOTO, Hiroki; KUGE, Yuji; ZHAO, Songji; NISHIJIMA, Ken-Ichi; EP2759538; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem