3-Bromobenzoic acid → 3-(4-methoxyphenyl)sulfanylbenzoic Acid

Participants

Reaction Steps

3-Bromobenzenecarboxylic acid (402 mg, 2 mmol), i-Pr2NEt (700 μL, 4 mmol) and dry 1,4-dioxane (8 mL) were put into a round-bottomed flask, and the round-bottomed flask with the resulting mixture therein was purged repeated three times with nitrogen gas. Next, Pd2(dba)3 (46 mg, 0.05 mmol), Xantphos (58 mg, 0.1 mmol) and 4-methoxythiophenol (246 μL, 2 mmol) were added to it, and this was purged repeatedly twice with nitrogen gas, and then heated under reflux for 6 hours. Next, the completion of the reaction was confirmed through high-performance liquid chromatography, then this was cooled to room temperature, and made to have a pH of 3 to 4 with acetic acid. The insoluble matter was removed through filtration, and the filtrate was concentrated. The resulting concentrate liquid was isolated and purified through flash column chromatography (developer: hexane/ethyl acetate=10/1) with silica gel serving as a carrier, thereby giving 432 mg (yield: 83%) of 3-(4-methoxyphenyl)sulfanylbenzenecarboxylic acid as a white solid.

Provenance & Evidence