Sulfuric Acid → HCID 49780356, compound

Participants

Reaction Steps

A solution of [2-(3-bromo-benzylamino)-phenyl]-methanol (0.180 mol) in DCM (50 mL) was added over a 5 hr period to a cooled (±−10 to −20° C.) solution of concentrated H2SO4 (500 mL). The ice-bath was then removed, and the mixture was stirred for one hour at rt. The reaction mixture was added to ice-water, cooled on ice, and alkalized with a 50% aqueous NaOH solution. The resulting mixture (±3 L) was extracted with DCM. The organic layer was separated, dried on MgSO4, filtered and the filtrate was concentrated in vacuo. A part (8 g) of this residue was purified via Supercritical Fluid Chromatography (SFC, column: Diacel AD-H 30×250 mm, mobile phase: 55% MeOH/45% CO2+0.2% isopropylamine, 40° C., 100 bar) to give 2 g of 10-bromo-6,11-dihydro-5H-dibenzo[b,e]azepine and 4.65 g of 8-bromo-6,11-dihydro-5H-dibenzo[b,e]azepine.

Provenance & Evidence