1,2-Dimethoxyethane → Tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate

Participants

Reaction Steps

To a mixed solution of ethylene glycol dimethyl ether 50 mL and water 15 mL of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 5.0 g were added vinylboronic acid pinacol ester 2.7 mL, potassium carbonate 2.3 g and tetrakis(triphenylphosphine)palladium(0) 0.80 g at room temperature sequentially, and it was heated and refluxed under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, toluene and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=20:1] to give tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 3.4 g of yellow oil.

Provenance & Evidence