Hydrochloric Acid → {4-[(Trifluoromethyl)sulfanyl]phenyl}boronic acid

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Reaction Steps

To a round-bottomed flask was added 4,4,5,5-tetramethyl-2-(4-trifluoromethylsulfanyl-phenyl)-[1,3,2]dioxaborolane (960 mg, 3.16 mmol) and sodium periodate (2.03 g, 9.48 mmol) in THF and water (4:1, 26 mL). The resulting suspension was stirred at rt for 30 min. HCl (1 N aq., 2.21 mL) was added to the suspension and the reaction mixture was stirred at rt for 18 h. The resulting precipitate was removed by filtration and washed with hexanes. The filtrate was diluted with water (25 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (10 mL×2), and the combined organic layers dried (Na2SO4) and concentrated to yield the title compound (512 mg, 73%).

Provenance & Evidence