Electric Literature of 729590-57-2,Some common heterocyclic compound, 729590-57-2, name is 4-(Benzyloxy)-1-bromo-2-chlorobenzene, molecular formula is C13H10BrClO, 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-2: Synthesis of 4-(benzyloxy)-l-(but-l-yn-l-yl)-2-chlorobenzene sealed tube/90 “C/12 h To a stirred solution of 4-(benzyloxy)-l-bromo-2-chlorobenzene (13 g, 43.91 mmol) in 130 mL of DMA in a sealed tube, were added copper iodide (0.833 g, 4.39 mmol) and cesium carbonate (28.63 g, 87.83 mmol) at room temperature. This mixture was degassed with three vacuum/N2 cycles, and were added but-l-yn-l-yltrimethylsilane (11 g, 87.83 mmol, Example-16, Step-2) followed by Pd(OAc)2 (1.079 g, 4.39 mmol) and dppf (2.4 g, 4.39 mmol). The pressure tube was sealed and heated at 90 C for 12 h. Upon completion by TLC, the reaction mixture was diluted with water (250 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified over 230-400 mesh silica gel column chromatography using 3% EtOAc in n-hexane to afford 4-(benzyloxy)-l-(but-l-yn-l-yl)-2-chlorobenzene (9.4 g, 80%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Benzyloxy)-1-bromo-2-chlorobenzene, its application will become more common.
Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (161 pag.)WO2016/196342; (2016); A1;,
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