Azobisisobutyronitrile → (4-bromo-5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester

Participants

Reaction Steps

A mixture of (5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester (480 mg), NBS (420 mg), and AIBN (30 mg) in CCl4 (18 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature, quenched with saturated sodium bicarbonate solution and extracted with dichloromethane (2×). The combined organics were washed with water, dried (Na2SO4), concentrated, and purified by flash column chromatography to give a light brown solid (420 mg) LCMS-ESI+ (m/z): [M+H]+ calcd for C16H18BrO4: 353.03. Found: 352.91.

Provenance & Evidence