Benzoyl Peroxide → 4,6-Dibromoisochroman-1-one

Participants

Reaction Steps

6-Bromo-3,4-dihydro-1H-isochromen-1-one (3.00 g, 13.2 mmol) was dissolved in CCl4 (150 mL) then added N-bromosuccinimide (2.352 g, 13.21 mmol) followed by benzoyl peroxide (0.0960 g, 0.396 mmol) and refluxed for 3 hrs. Filtered and concentrated then chromatographed through a 120 g ISCO Redi-sep. column and eluted with 0-25% ETOAc/Hexane to yield 4,6-dibromo-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 306.9 [M+1]+; 1H-NMR (500 MHz, CDCL3) δ ppm 8.03 (d, J=8.9 Hz, 1H), 7.69 (d, J=7.9 Hz, 1H), 7.68 (s, 1H), 5.32 (t, J=3 Hz, 1H), 4.72-4.81 (q, 1H).

Provenance & Evidence