1,2-Dimethoxyethane → 4-(Thiophen-3-yl)aniline

Participants

Reaction Steps

An aqueous sodium carbonate solution and tetrakis triphenylphosphine palladium were added to a DME solution of 3-bromothiophene and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, and the mixture was refluxed under heating for 6 hours with argon atmosphere. After cooling to room temperature, the reaction mixture was added with ethyl acetate and water to separate an organic layer, which was then washed and dried. The solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography, to obtain 4-(3-thienyl)aniline (pale yellow solid). Electron Impact-MS (M)+: 175.

Provenance & Evidence