N-bromobutanimide → HCID 68979485, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6,11-dihydro-11-methyl-5H-dibenzo[b,e]azepine (4) (8 g, 38.3 mmol) in aceton (1500 mL) was cooled to 0° C. and NBS (N-bromosuccinamide; 6.81 g, 38.3 mmol) was added. The reaction mixture was stirred for 20 min at 0° C., quenched by addition of aqueous NaHCO3 (300 mL) and concentrated under reduced pressure. The product was extracted into ethyl acetate which was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=8:2) to give 2-bromo-6,11-dihydro-11-methyl-5H-dibenzo[b,e]azepine (4, R8═Br; 32 g, 97%) Data: (m/z)=288/290 (M+H)+.

Provenance & Evidence