Ethyl 4-bromo-2-butenoate → HCID 46344355, compound

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Reaction Conditions

Reaction Steps

420 ml of ethanol are introduced into a 3 litre reactor, with magnetic stirring, cooled to 0° C., and 3.8 g (0.166 mol) of sodium are added slowly, in small portions, followed by successive and dropwise addition of 40 g (0.166 mol) of N-(5-chloro-2-hydroxyphenyl)trifluoroacetamide and 40 g (0.155 mol) of 75% pure ethyl 4-bromo-2-butenoate, and the mixture is heated at 85° C. for 2 hours. The solvent is evaporated off and the residue is taken up in 100 ml of water and 40 ml of 1N sodium hydroxide and extracted with diethyl ether. The organic phase is separated out, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. 28.58 g of product are obtained, which product is purified by chromatography on a column of silica gel, eluting with a cyclohexane/isopropyl ether (1/1 ratio) mixture.

Provenance & Evidence