N-bromobutanimide → HCID 67248702, compound

Participants

Reaction Steps

To a solution of Example 112A (1.30 g, 4.23 mmol) in acetic acid (20 mL) was added N-bromosuccinimide (0.828, 4.65 mmol). The reaction stirred for 16 hours. The reaction solution was concentrated, then partitioned between NaOH (1 M) and dichloromethane. The dichloromethane layer was separated and concentrated onto silica gel. Purification via flash chromatography (30-100% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.22-7.38 (m, 6 H), 7.07 (d, J=2.37 Hz, 1 H), 7.01 (d, J=8.81 Hz, 1 H), 3.50-3.58 (m, 2 H), 3.24-3.30 (m, 1 H), 3.05-3.17 (m, 1 H), 2.91-3.01 (m, 1 H), 2.71-2.86 (m, 2 H), 2.52-2.61 (m, 1 H), 2.05-2.25 (m, 2 H), 1.90 (d, J=13.22 Hz, 1 H); MS (APCI+) m/z 386, 388 (M+H)+.

Provenance & Evidence