Ethyl 3-(2-BroMo-6-nitrophenyl)-2-oxopropanoate synthesis

Yield:-

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide at 0; for 4 h;

Steps:

Synthesis of ethyl 3-(2-bromo-6-nitrophenyl)-2-oxopropanoate 7

NaH (0.167 g, 6.94 mmol, 1.5 eq) was dissolved in 10 mL of anhydrous DMF and cooled to 0 °C. The solution of 1-bromo-2-methyl-3-nitrobenzene 5 (1.00 g, 4.63 mmol, 1.0 eq) and diethyl oxalate 6 (1.25 mL, 9.26 mmol, 2.0 eq) in the 10 mL anhydrous DMF were added into the reaction mixture dropwise at 0 °C. The reaction was stirred for 4 hours until the consumption of starting material 5 as monitored by TLC. After completion, the reaction mixture was poured into 40 mL of cooled 4 M HCl and extracted with EtOAc (2x20 mL). The organic layer was combined, washed with water, dried with MgSO₄, filtered, evaporated to dryness to afford 7, and used directly in the next step without further purification.

References:

Clausen, Rasmus P.;Hansen, Kasper B.;Rouzbeh, Nirvan;Zhao, Fabao [Tetrahedron Letters,2020] Location in patent:supporting information