N-bromobutanimide → HCID 118044990, compound

Participants

Reaction Steps

To a solution of protected 2-aminothiophene 14 (2.5 g; 8.33 mmol), N-bromosuccinimide (1.55 g; 8.74 mmol) and benzoyl peroxide (20 mg) in CCl4 (50 ml) was heated at reflux temperature for 20 h under argon atmosphere. The CCl4 was evaporated under reduced pressure and the residue was extracted with dichloromethane (3×50 ml). The combined organic phases were washed with a saturated solution of NaHCO3, dried over magnesium sulfate and the solvent was evaporated under reduced pressure Purification by column chromatography (silica, eluent CH2Cl2) afforded 15 (1.9 g, 60%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δH 3.72 (s, 3H); 4.66 (s, 2H); 7.51 (s, 1H); 7.84 (m, 2H); 7.97 (m, 2H).

Provenance & Evidence