N-bromobutanimide → HCID 59807115, compound

Participants

Reaction Steps

A solution of compound 2 (4.15 g, 14.390 mmol) in dry DMF (30 mL) was treated with NBS (2.56 g, 14.390 mmol) in dry DMF (20 mL) at 0° C. and resulting solution was stirred at same temperature for 3 h. The reaction was diluted with water (150 mL) and product was extracted into ethyl acetate (3×30 mL). The combined ethyl acetate layer was washed with water (2×25 mL), brine (25 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (ethyl acetate:hexanes, 1:4) to obtain compound 3 (5.12 g, 97%) as a syrup. 1H NMR (CDCl3) δ 7.18-7.07 (m, 2H), 6.33 (d, 1H, J=8.7 Hz), 4.13-3.99 (m, 1H), 3.68-3.26 (m, 6H), 2.94 (t, 2H, J=8.1 Hz), 2.17-1.99 (m, 2H), 1.46 (s, 9H); ESI-MS (m/z, %): 390 (MNa+, 6), 368 (MH+, 3), 313, 311(100).

Provenance & Evidence