Triethylamine → Ethyl 3-aminobenzo[b]thiophene-2-carboxylate

Participants

Reaction Steps

2-Fluorobenzonitrile (0.61 g, 5 mmol), ethyl thioglycollate (0.60 g, 5 mmol) and NEt3 (1.52 g, 15 mmol) are stirred in DMSO (5 mL) at 100° C. under N2 for 3 h. The reaction mixture is poured onto ice-water (50 mL), and the solid is collected by suction filtration, rinsed with water, and air dried to give ethyl 3-aminobenzothiophene-2-carboxylate (0.78 g, 70%) as a grey-brown solid. 1H NMR (DMSO) δ8.14 (1H, d, J=7.7 Hz), 7.88 (1H, d, J=8.1 Hz), 7.50 (1H, dt, Jd=1.2 Hz, Jt=7.5 Hz), 7.39 (1H, dt, Jd=1.2 Hz, Jt=7.6 Hz), 7.17 (2H, brs), 4.26 (2H, q, J=7.1 Hz), 1.29 (3H, t, J=7.1 Hz).

Provenance & Evidence