Phenylboronic Acid → HCID 59707359, compound

Participants

Reaction Steps

A Schlenk tube was charged with 5-bromo-2,4-bis-methoxymethoxy-benzoic acid methyl ester (3) (503 mg, 1.5 mmol), phenylboronic acid (272 mg, 2.3 mmol), Pd(OAc)2 (22 mg, 0.1 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (82 mg, 0.2 mmol), K3PO4H2O (4.70 g, 34.0 mmol). The reaction tube was evacuated and backfilled with N2 (×3). Toluene (10 mL, anhydrous and sure seal bottle from Aldrich) was added. The reaction was stirred at room temperature for 10 min and heated at 105° C. (preheated oil bath) for 24 h. The reaction mixture was allowed to cool to room temperature and diluted with EtOAc (50 mL) and water (70 mL). The aqueous phase was extracted with EtOAc (40 mL×3) and the combined organic layers were washed with water and brine and dried over MgSO4. The purification of the concentrated crude product by column chromatography (25% EtOAc in Hexane) afforded the title product as colorless oil (460 mg, 93%).

Provenance & Evidence