N-bromobutanimide → HCID 70885920, compound

Participants

Reaction Steps

To a solution of 4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (5 g, 13.68 mmol) in CHCl3 (133 mL) at 0° C. was added N-bromosuccinimide (2.44 g, 13.68 mmol) over a period of 20 min. While warming up to room temperature, the resulting solution was stirred in the absence of light overnight. The reaction was quenched with a saturated aqueous solution of Na2S2O3. The resulting mixture was extracted with CH2Cl2 (3×) and the combined organic fractions were dried with MgSO4. After filtration and evaporation of the solvent, the residue was subjected to column chromatography (silica, n-hexane/CH2Cl2 4:1). Final recrystallization from ethanol yielded 2-bromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a white powder (5.6 g, 92%).

Provenance & Evidence