Ethyl 2-bromopropionate → Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate

Participants

Reaction Steps

To a solution of 0.256 g of sodium in 30 ml of ethanol is added 2 g of 4-(4-chloroanilinomethyl)phenol, and 2.02 g of ethyl 2-bromopropionate is further added dropwise at room temperature. The mixture is thereafter refluxed under heating for 5.5 hours. The ethanol is distilled off from the reaction mixture, 20 ml of water is added to the residue, and the diluted residue is extracted with ether. The extract is washed twice with a saturated aqueous solution of sodium chloride and then dried. After distilling off the solvent from the dried extract, the residue (2.9 g) is purified by column chromatography, using 60 g of silica gel and chloroform as a developer, to give 2.1 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate as an oily product.

Provenance & Evidence