Triisopropyl borate → HCID 59631451, compound

Participants

Reaction Conditions

Reaction Steps

The (2-bromo-4-methylphenyl)(methyl)sulfane (700 mg, 3.20 mmol) was dissolved in THF (5.0 mL) and cooled to −78° C. To the cooled solution was added n-butyl lithium (2.2 mL, 3.60 mmol) dropwise. The reaction was stirred for 2 min at −78° C. then the triisopropyl borate (0.82 mL, 3.56 mmol) was added dropwise and the reaction mixture was allowed to warm to 0° C. over a period of approximately 90 min. The reaction was quenched by addition of 1N HCl solution and was stirred for 5 min. The mixture was then extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (1×30 mL), brine (1×30 mL) and dried over magnesium sulfate. The crude product was then triturated with EtOAc and hexanes to give 5-methyl-2-(methylthio)phenylboronic acid. The mother liquor was purified by medium pressure chromatography (silica gel, 0 to 30% EtOAc:hexanes) to give more desired product. Mass Spectrum (ESI) m/e=183.1 (M+1).

Provenance & Evidence