N-bromobutanimide → HCID 10150003, compound

Participants

Reaction Steps

The title compound was prepared by reacting 1-(Acetyloxy)-6H-dibenzo[c,h]chromen-8-yl acetate (510 mg, 1.46 mmol), NBS (315 mg, 1.77 mmol), and anhydrous DMF (30 ml) at room temperature for 1.5 hours according to method B. The reaction was concentrated under reduced pressure, dissolved in MeOH (30 ml), and NH3 was bubbled in for 1.5 h while acetate removal was monitored by LC-MS. The reaction was concentrated to a dark sludge and purified by silica chromatography (1:1 EtOAc:hexanes) to afford 340 mg (68%) of product as a tan solid. Mp: decomposes above 130° C.; 1H NMR (500 MHz, DMSO-d6) δ 5.23 (2H, s), 6.72 (1H, d, J=1.9 Hz), 6.81 (1H, dd, J=8.2 Hz, 2.5 Hz), 6.92 (1H, dd, J=7.7 Hz, 1.1 Hz), 7.33 (1H, t, J=8.0 Hz), 7.64 (1H, dd, J=8.5 Hz, 1.1 Hz), 7.68 (1H, d, J=8.5 Hz), 8.01 (1H, s), 9.78 (1H, s), 10.15 (1H, s); MS m/z341/343 (Br pattern) (M−H+).

Provenance & Evidence