Benzyl Bromide → N-ethyl-3-benzyloxy-4-nitrobenzamide

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Reaction Steps

N-Ethyl-3-hydroxy-4-nitrobenzamide (5.23 g, 24.9 mmol) obtained in Example 312a) was dissolved in anhydrous DMF (100 ml), potassium carbonate (4.47 g, 32.3 mmol, 1.3 eq.) was added at room temperature, benzyl bromide (3.17 ml, 26.1 mmol, 1.05 eq.) was added dropwise, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with 5% aqueous sodium hydrogen carbonate solution (200 ml) and extracted with ethyl acetate-hexane (3:1, 200 ml and 150 ml). The organic layer was washed sequentially with 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (5.42 g, 18.1 mmol, 72.5%).

Provenance & Evidence