Hydrochloric Acid → 2-(4-Bromophenyl)thiophen-3-amine

Participants

Reaction Steps

A solution of (tert-butoxy)-N-[2-(4-bromophenyl)(3-thienyl)]carboxamide (10.8 g, 0.3 mmol, preparation 7) in ethyl acetate (75 mL) at 0° C., is treated dropwise with 244 mL (8 mL/mmol) of freshly prepared 1N HCl in ethyl acetate and the mixture is stirred at room temperature overnight. The white precipitate is dissolved with H2O (100 mL) and neutralized with a NaHCO3 saturated solution. The mixture is then extracted with ethyl acetate (3×100 mL) and the combined organics are dried and concentrated to give a slightly colored solid. Purification of the crude material by flash chromatography (Silica gel-Hexane/AcOEt 49:1 then 9:1) furnishes 5.7 g (74%) of title compound as a pale yellow solid.

Provenance & Evidence