Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.
Step A: methyl 2-cyanoacetate (23 g, 232 mmol) was addeddropwise to a suspension of sodium hydride (60percent, 2.79 g,69.7 mmol) in DMF (100 mL) and THF (100 mL) at 0 C, and thereaction mixture was warmed to rt and stirred at rt for 30 min.((2-Bromoethoxy)methyl)benzene (10 g, 46.5 mmol) was added,and the reaction mixture was stirred at rt for 12 h. Water wasadded and the aqueous layer was extracted with ether (3). Thecombined organic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was evaporatedto give the crude product. Excessive methyl 2-cyanoacetate wasremoved by distillation under high vacuum at 120?130 C, andremaining residue was purified by silica gel chromatography elutingwith 0?50percent EtOAc/hexanes to give methyl 4-(benzyloxy)-2-cyanobutanoate (8 g, 74percent) as a colorless liquid. 1H NMR(300 MHz, CDCl3) d 7.3 (m, 5H), 4.51 (s, 2H), 3.70 (s, 3H), 3.6?3.9(m, 3H), and 2.3 (m, 2H). LC/MS m/z: (M+H)+ calcd forC13H16NO3, 234.11; found 234.4. Step B: To a suspension of sodiumhydride (60percent, 9 g, 225 mmol) in THF (170 mL) and DMF (170 mL)was added methyl 4-(benzyloxy)-2-cyanobutanoate (35 g,150 mmol) at 0 C, and the reaction mixture was stirred at rt for30 min. ((3-Bromopropoxy)methyl)benzene (37.8 g, 165 mmol)was added, and the reaction mixture was stirred at rt for 12 h.Water was added and the aqueous layer was extracted with ether(3). The combined organic layers were washed with brine, driedover anhydrous sodium sulfate, and filtered, and the filtrate wasevaporated to give the crude product. The crude product was purifiedby silica gel chromatography eluting with 0?40percent EtOAc/hexanesto give 22 (40 g, 70percent) as a colorless oil. 1H NMR (400 MHz,CDCl3) d 7.3 (m, 10H), 4.48 (2H, s), 4.47 (2H, s), 3.7 (m, 2H), 3.57(3H, s), 3.48 (m, 1H), 2.42 (m, 1H), 1.8?2.1 (m, 4H), and 1.6 (m,1H). LC/MS m/z: (M+H)+ calcd for C23H28NO4, 382.20; found 382.4.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
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;,
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