N-bromobutanimide → HCID 90285707, compound

Participants

Reaction Steps

To a solution of 4,4,8,8,12,12-hexamethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (2.10 g, 4.27 mmol) in CHCl3 (77 mL) at 0° C. was added N-bromosuccinimide (0.761 g, 4.27 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 2:3). Final recrystallization from ethanol yielded 2-bromo-4,4,8,8,12,12-hexamethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a white powder (1.87 g, 77%).

Provenance & Evidence