N-bromobutanimide → HCID 58670137, compound

Participants

Reaction Steps

To a solution of 1B (85 mg, 0.5 mmol) in DMF (1 mL) at RT was added N-bromosuccinimide (89 mg, 0.5 mmol). The reaction was stirred at RT for 16 h. After this time, no starting material was detected by LC-MS. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with saturated NaCl, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica gel (10 g) column chromatography, eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as a light brown foam (100 mg, 80%). LC/MS (method A): retention time=2.96 min, (M+H)+=249. 1H NMR (CDCl3, 400 MHz): δ 7.80-7.91(m, 2H), 7.50 (d, J=8.2 Hz, 1H), 7.38-7.44 (m, 2H), 7.31-7.35 (m, 1H), 7.05 (d, J=8.2 Hz, 1H), 4.15 (s, 2H).

Provenance & Evidence