4-Nitrobenzyl bromide → Diethyl 2-(4-nitrobenzyl)-2-methylmalonate

Participants

Reaction Steps

Diethyl methyl malonate (1.60 ml, 9.25 mmol) was added to a freshly prepared solution of sodium ethoxide solution [(sodium (212 mg, 9.25 mmol) in EtOH (20 ml)] and stirred for 1 h. 4-Nitrobenzyl bromide (2.00 g, 9.25 mmol) was added dropwise to the reaction mixture and stirred for 6 h at reflux. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between water and CHCl3. The separated organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. This was purified by column chromatography over silica gel (100-200 mesh) using 5% ethyl acetate in petroleum ether as eluent to afford 850 mg (29.7%) of diethyl 2-(4-nitrobenzyl)-2-methylmalonate as oily liquid.

Provenance & Evidence