Hydrochloric Acid → 4'-Acetamidomethyl-2'-methylbiphenyl-4-carboxylic acid

Participants

Reaction Steps

4-Bromo-3-methylbenzylamine (EP 532266) (7.36 g, 0.037 mol) was dissolved in 1,2-dimethoxyethane (DME) (180 ml), with stirring, and was treated with 4-boronobenzoic acid (6.14 g, 0.037 mol), followed by a solution of sodium carbonate (17.65 g, 0.167 mol) in water (180 ml). The reaction mixture was then flushed with argon and tetrakis (triphenylphosphine)palladium (O) (1.00 g) was added. The reaction mixture was then heated to reflux under argon. After 16 h, the reaction mixture was allowed to cool and the DME was removed by evaporation under reduced pressure. The aqueous residue was then diluted with water (~200 ml) and washed with EtOAc (2×150 ml). The aqueous layer was then treated with acetic anhydride (6.98 ml, 0.074 mol) and stirred for 1 h at room temperature. The resulting pale brown solution was filtered through kieselguhr to give a pale yellow solution, which was acidified to pH 5 using conc. HCl to give an off white precipitate. This was filtered off, washed with water and dried in vacuo to give the title compound as on off white solid (5.85 g, 56%).

Provenance & Evidence