Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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 stirred suspension of 4-chloro-3-hydroxy-5-nitrobenzamide (30 g, 139 mmol) and potassium carbonate (57.4 g, 416 mmol) in DMF (200 mL) under nitrogen was added at room temperature a solution of ((3-bromopropoxy)methyl)benzene (47.6 g, 208 mmol) dropwise during 1 minute. The reaction mixture was stirred at 80 °C overnight. The reaction mixture was cooled to room temperature and quenched by the addition of 200 mL of water. The aqueous phase was then extracted with DCM (3×100 mL). The combined organic layer was washed with water (4×200 mL) and brine (200 mL), dried, and concentrated under vacuum. The crude product was purified by silica gel chromatography (100 g column, 1:2 petroleum ether/EtOAc). The appropriate fractions were pooled and concentrated to afford 3-(3-(benzyloxy)propoxy)-4-chloro-5-nitrobenzamide (33 g, 90 mmol, 65.3percent yield) as a yellow solid. LCMS (m/z): 365 [M + H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route ((3-Bromopropoxy)methyl)benzene, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FOSBENNER, David T.; GRAYBILL, Todd L.; KANG, Jianxing; KING, Bryan W.; LAN, Yunfeng; LEISTER, Lara Kathryn; MAHAJAN, Mukesh K.; MEHLMANN, John F.; MORALES-RAMOS, Angel I.; PESIRIDIS, George Scott; RAMANJULU, Joshi M.; ROMANO, Joseph J.; ROMERIL, Stuart Paul; SCHULZ, Mark J.; ZHOU, Huiqiang; (372 pag.)WO2019/69270; (2019); A1;,
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