Electric Literature of 653-92-9,Some common heterocyclic compound, 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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.
General procedure: To a solution of (2) in 1 ,4-dioxane (4 mL) were added 1 ‘1 [bis(diphenylphosphino) ferrocene] dichloropalladium(ll) (0.2 eq), Na2C03 (8 eq) and one of the following regents heteroarylboronic acid or heteroaryiboronic acid pinacol ester or heteroarylboronic MIDA ester (2 eq) in a microwave tube. After addition of H20 (1 mL), the tube was sealed and the reaction mixture was stirred at 90C for 16 h. The mixture was allowed to cool to room temperature, was filtered through celite and MgS04 and the filter was repeatedly washed with ethyl acetate. After removing the solvent under reduced pressure, the crude residue was dissolved in saturated aqueous Na2C03 solution. The aqueous layer was extracted three times with CHCI3 and the combined organic layers were washed with saturated, aqueous NaCI solution and dried over Na2S04). The organic solvent was removed under reduced pressure and the residue was purified by preparative HPLC to obtain the appropriate target compound
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-fluorobenzoate, its application will become more common.
Reference:
Patent; FRIEDRICH-ALEXANDER-UNIVERSITAeT ERLANGEN-NUeRNBERG; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BANERJEE, Ashutosh; BARTUSCHAT, Amelie; EITEL, Katrin; GMEINER, Peter; HEINRICH, Markus; HOFMANN, Josefa; HUeBNER, Harald; RAMPP, Hannelore; SCHAAKE, Benjamin; KOBILKA, Brian; SUNAHARA, Roger; CLARK, Mary Joyce; FISH, Inbar; SHOICHET, Brian; (90 pag.)WO2019/110521; (2019); A1;,
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