Hydrochloric Acid → 2-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene

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Reaction Steps

14.1 g (35.0 mmol) of propyltriphenylphosphonium bromide are initially introduced in 150 ml of THF at 0° C., and 3.93 g (35.0 mmol) of potassium tert-butoxide dissolved in 50 ml of THF are added. After 1 h at this temperature, 9.0 g (28.6 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added as a solution in 300 ml of THF, and the batch is stirred at RT for 19 h. Water and 2 N hydrochloric acid are added to the mixture, and the batch is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). 2-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene is obtained as a reddish solid.

Provenance & Evidence