Iodine → 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl ester

Participants

Reaction Steps

861 mg of 4-(2-bromophenoxy)-butyric acid ethyl ester and 4.8 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) are dissolved in 11 ml of toluene, mixed with 70 mg of tetrakis-(triphenylphosphine)-palladium and heated with stirring and under argon atmosphere for 1 hour to 120° C. (bath temperature). After cooling to room temperature, the reaction mixture is diluted with 9 ml of diethyl ether and mixed at 0° C. with a solution of 1.53 g of iodine in 7 ml of diethyl ether. The mixture is stirred for 2 hours at 0° C. and allowed to stand overnight in a refrigerator. The batch is concentrated by evaporation and the residue is chromatographed on silica gel with n-hexane/ethyl acetate=95/5. 810 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]-butyric acid ethyl ester is obtained as an oily crude product, which is further reacted without further purification.

Provenance & Evidence