These common heterocyclic compound, 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)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. Application In Synthesis of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene
Synthesis of compound 11C50H49CIO6 M = 781.37 g.moF1 Mass: ESI+): 798.20 (M + H20)Under inert atmosphere, Mg powder (265mg, 10.9mmol, 2.4eq) was charged into a three necked flask, followed by addition of a portion of 1/3 of a solution of the 4- bromo-l-chloro-2-(4-ethylbenzyl)benzene (2.95g, 9.1mmol; 2eq) in dry THF (25mL) and 1 ,2-dibromoethane (10 mol % of Mg; 85mg; 0.45mmol). The mixture was heated to reflux. After the reaction was initiated (exothermic and consuming of Mg), the remaining solution of 2-(4-ethylbenzyl)-4-bromo-l-chlorobenzene in dry TFIF was added dropwise. The mixture was then allowed to react for another one hour under gentle reflux until most of the Mg was consumed.The above Grignard reagent was added dropwise into the solution of cyclohexenone 8 (2.42g, 4.53mmol, leq) in dry THF (25mL) under inert atmosphere at room temperature (about 25C), then allowed to react for 3h. A saturated aqueous solution of ammonium chloride was added into the mixture to quench the reaction. The mixture was extracted with Et20, washed with brine, dried over sodium sulphate, filtered and concentrated. The residue was purified on silica gel chromatography (cyclohexane/ethyl acetate 100:0 to 80:20) to afford the target compound 11 as a yellow oil (3.01g, 86%).
The synthetic route of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TFCHEM; DELIENCOURT-GODEFROY, Geraldine; LOPES, Lenaig; WO2012/160218; (2012); A1;,
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