N-bromobutanimide → HCID 59807130, compound

Participants

Reaction Conditions

Reaction Steps

A solution of compound 3 (0.73 g, 2.99 mmol) in DMF (5 mL) was treated with a solution of NBS (0.53 g, 2.99 mmol) in DMF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and stored at 0° C. overnight. The reaction mixture was diluted with H2O (100 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4) and concentrated. The product was filtered through a short plug of silica gel (2.0 N NH3 in MeOH:CH2Cl2, 2.5:97.5) to give compound 4 (0.915 g, 95.3%) as a yellow oil. 1H-NMR (DMSO-d6) δ 1.56 (m, 4H), 1.72 (m, 4H), 1.96 (td, 2H, J=10.9, 2.2 Hz), 2.15 (s, 3H), 2.65 (m, 2H), 2.76 (m, 2H), 2.93 (m, 2H), 3.14 (m, 1H), 6.83 (d, 1H, J=8.5 Hz), 7.19 (td, 2H, J=8.6, 2.4 Hz); EI-MS (m/z, %) 324 (M+, 14) 322 (M+, 14), 98 (25), 97 (100), 96 (25), 71 (38).

Provenance & Evidence