Electric Literature of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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 (£ ethyl 3-(4-bromophenyl)acrylate (10.0 g, 39.2 mmol) in THF (150 mL) was slowly added at -78 C a solution of DIBA1-H (86 mL of 1M solution in hexanes, 86.0 mmol). The resulting solution was then allowed to slowly warm to 0 C, after which a further 10 mL of DIBA1-H solution was added. TLC analysis indicated complete reaction and the mixture was re-cooled to -78 C. MeOH was then slowly added to quench the remaining reducing agent and the mixture allowed to warm back to rt over 30 minutes. The resulting mixture was poured into a saturated aqueous solution of Rochelle’s salt and then extracted with EtOAc. The organic phase was separated, dried (MgSO i), filtered and the filtrateconcentrated in vacuo. The crude product thus obtained was purified on silica eluting with a gradient of 0 to 35% EtOAc in hexanes to afford 6.0 g (71%) of (£)-3-(4-bromophenyl)prop-2-en-l-ol.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.
Reference:
Patent; INCEPTION 2, INC.; STOCK, Nicholas, Simon; CHEN, Austin, Chih-Yu; BRAVO, Yalda, Mostofi; JACINTHO, Jason, Duarte; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; CLARK, Ryan, Christopher; TRUONG, Yen, Pham; WO2013/134562; (2013); A1;,
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