m-Chloroperbenzoic acid → 8-Bromo-2-chloro-5h,11h-dibenzo[b,f]azocine-6-12-dione

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Reaction Steps

To a solution 3-Bromo-8-chloro-5,10-dihydro-indeno[1,2-b]indole (4.2 g, 13 mmol) in chloroform (150 mL) and 5% aqueous NaHCO3 (56 mL) was added mCPBA (7.5 g, 43 mmol) in chloroform (150 mL) dropwise over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The resulting oil was triturated with ether and filtered. The filter cake was washed with ether and dried in vacuo to give 8-Bromo-2-chloro-5H,11H-dibenzo[b,f]azocine-6-12-dione (2.0 g, 43%). 1HNMR (CDCl3) δ 7.67 (d, 1H, J+2.20 Hz), 7.59 (d, 1H, J=1.76 Hz), 7.42 (dd, 1H, J=7.92, 1.76 Hz), 7.32 (dd, 1H, J=8.01, 2.20 Hz), 7.02 (m, 2H), 4.44 (d, 1H, J=15.40 Hz), 3.85 (d, 1H, J=14.96 Hz). HPLC Rt=3.65 min.

Provenance & Evidence