Hydrogen Peroxide → HCID 57962486, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl (3-bromo-5-vinylphenyl)carbamate (0.80 g, 2.7 mmol) in tetrahydrofuran (2.7 mL) was treated with 9-BBN in tetrahydrofuran (16.1 mL, 8.1 mol) dropwise and stirred for 2 h. The reaction mixture was cooled to 0° C. and treated with ethanol (5 mL), 3 M sodium hydroxide (3.2 mL) and 9 M hydrogen peroxide (3 mL) dropwise. The reaction mixture was heated at 50° C. for 30 min, cooled to 20° C., poured into brine (25 mL), and extracted with ethyl acetate (100 mL). A small amount of water was added to dissolve the solids that were insoluble in the brine. The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude tan oil. This material was purified by flash column chromatography to give the desired product (0.66 g, 78%) as a colorless foam. LCMS for C9H11BrNO3 ([M-(t-Bu)+H]+H)+: m/z=259.9, 261.8.

Provenance & Evidence