Hydrochloric Acid → 3-(3-Methoxycarbonylphenyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

3-Iodobenzoic acid (1.0 g, 4.03 mmol, 1 equiv.), 3-(methoxycarbonyl)phenylboronic acid (0.73 g, 4.03 mmol, 1 equiv.), and Pd(OAc)2 (27 mg, 0.12 mmol, 0.03 equiv.) were mixed in DMF (10 mL) at RT with stirring, followed by the addition of 1.5M cesium carbonate (8.06 mL, 1.16 mmol, 3 equiv.). The mixture was heated at 40° C. for 4 hours. At the conclusion of this period, the reaction was worked up by adding water and adjusting the pH to 3 with 1N HCl. The aqueous mixture was extracted (3×) with EtOAc/THF. The organic layers were rinsed (3×) with water. The organic layer was dried over sodium sulfate and concentrated to give an off-white solid. The solid was stirred in hexanes (10 mL), filtered and dried under high vacuum to give 3′-(methoxycarbonyl)biphenyl-3-carboxylic acid (860 mg, 3.36 mmol, 83% yield) as a white solid. MS (ESI+)=257.23 (M+H)+.

Provenance & Evidence