Hydrochloric Acid → Ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

20 g of ethyl 4-nitrophenylacetate are dissolved in 30 ml of DMF and added dropwise to a suspension of 4 g of sodium hydride in 20 ml of DMF with ice-cooling. 8.5 ml of dibromoethane are subsequently added, and the mixture is stirred at 55° C. for 1 h. A further 5 g of sodium hydride and 8.5 ml of dibromoethane are added with ice-cooling, and the mixture is then stirred at 50° C. for 2 h. After cooling, the reaction mixture is stirred into a mixture of 100 ml of 1 N hydrochloric acid and 200 g of ice. The mixture is washed four times with 100 ml of diethyl ether each time, the combined organic phases once with 100 ml of sodium chloride solution, dried over sodium sulfate and, after filtration, evaporated to dryness in vacuo. The residue is purified by column chromatography (reversed phase). Yield: 8.5 g (38%) of ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate; LC-MS retention time: 2.01 min (“nonpolar” gradient);

Provenance & Evidence