N-bromobutanimide → HCID 21029604, compound

Participants

Reaction Steps

A solution of compound 2 (1.12 g, 5.176 mmol) in dry DMF (10 mL) was treated with NBS (0.92 g, 5.176 mmol) in dry DMF (5 mL) at 0° C. over a period of 5 min. and stirring was continued at same temperature for 3 h. The reaction was diluted with water (100 mL) and product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 3:97) to obtain compound 3 (1.15 g, 76%) as a syrup. 1H NMR (DMSO-d6) δ 7.14-7.06 (m, 2H), 6.37 (d, 1H, J=8.4 Hz), 3.35-3.24 (m, 3H, merged with water peak), 2.93-2.80 (m, 4H), 2.16 (s, 3H), 2.00-1.88 (m, 2H), 1.64-1.55 (m, 4H); EI-MS (m/z, %): 293, 295 (M+, bromine isotope, 47), 98 (59), 97 (100), 71 (47).

Provenance & Evidence