Hydrochloric Acid → Methyl 2-(4-fluoroanilino)-4-iodobenzoate

Participants

Reaction Steps

To toluene 20 mL suspension of 4-fluorophenylboronic acid 1.4 g, anhydrous copper(II) acetate 0.35 g and myristic acid 0.89 g was added 2,6-lutidine 0.76 mL, and it was stirred at room temperature for 5 minutes. Methyl 2-amino-4-iodobenzoate 1.8 g was added to the reaction mixture, and it was stirred at room temperature for 3 hours. 4-fluorophenylboronic acid 0.45 g and anhydrous copper(II) acetate 0.35 g were added to the reaction mixture, and it was stirred at room temperature for 8 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. 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 [eluent; hexane:ethyl acetate=10:1] to give methyl 2-(4-fluoroanilino)-4-iodobenzoate 0.63 g of pale yellow solid.

Provenance & Evidence