N-bromobutanimide → Ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylate

Participants

Reaction Steps

To a solution of 1c (760 mg, 3.44 mmol) in CHCl3 (10 mL) was added N-bromosuccinimide (673 mg, 3.78 mmol). The resultant mixture was stirred for 1 h, then mixed with saturated NaHCO3 solution (100 mL), and extracted with methylene chloride (100 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then provided the title compound (930 mg, 90%) as a yellow solid: MS (ES) m/z 300 (M+H)+; 1H NMR (400 MHz, CDCl3) δ7.96 (d, J=8.8 Hz, 1H), 7.63 (s, 1H), 7.42 (d, J=8.8 Hz, 1H), 6.52 (brs, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H).

Provenance & Evidence