Acetic Acid → ((r)-7-Bromo-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

A round-bottom flask containing ((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester (0.338 g, 1.20 mmol) was fitted with a stirbar and septa. Acetic acid (glacial, 5 mL) and bromine (0.37 g, 2.3 mmol) were added, in that order, giving a solution that was stirred at room temperature for 1.5 hours. The reaction was then poured into ethyl acetate (50 mL) and washed with saturated aqueous NaHCO3 solution (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (10% to 50% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence