N-bromobutanimide → HCID 74892031, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added 6-amino-3,4-dihydro-1(2H)-naphthalenone (5.30 g, 32.9 mmol) and DCM (329 mL) and the mixture was cooled to 0° C. N-bromosuccinimide (5.85 g, 32.9 mmol) was added portionwise over 1 hour. The mixture then was stirred at 0° C. for 3 hours. The reaction was quenched with aqueous sodium bicarbonate (100 mL) and then extracted with DCM (3×100 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The product was purified by silica gel chromatography using a gradient solvent system of 0-65% EtOAc/Hexanes. Concentration of the product-containing fractions yielded 6-amino-5-bromo-3,4-dihydronaphthalen-1(2H)-one (7.8 g, 87%) as a light tan solid. MS ESI calcd for C10H10BrNO 240 [M+H]+. found 240.

Provenance & Evidence