Ethyl 2-((2-bromo-6-nitrophenyl)thio)acetate → 8-Bromo-2H-benzo[b][1,4]thiazin-3(4H)-one

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Reaction Conditions

Reaction Steps

A mixture of ethyl 2-((2-bromo-6-nitrophenyl)thio)acetate (3.64 g, 11.37 mmol) and iron (6.35 g, 114 mmol) in acetic acid (56.8 ml) was stirred at 90° C. for 1.5 h and at room temperature overnight. The mixture was filtered through CELITE®, washed with methanol, followed by hot CHCl3:MeOH:AcOH (1:1:1) till most of the compound came off the CELITE®. The filtrated was concentrated and re-dissolved in EtOAc. The organic solution was washed with water, dried over MgSO4, filtered, and concentrated to afford the title compound (2.59 g, 90% yield). LCMS, [M+H]+=246.0. 1H NMR (400 MHz, DMSO-d6) δ 7.27 (dd, J=8.0, 1.0 Hz, 1H), 7.10 (t, J=8.0 Hz, 1H), 6.97 (dd, J=8.0, 1.0 Hz, 1H), 3.53 (s, 2H).

Provenance & Evidence