2-Chloroaniline → 5-bromo-N-(2-chlorophenyl)thiophene-2-carboxamide

Participants

Reaction Steps

A mixture of 5-bromo-thiophene-2-carboxylic acid (5) (207 mg, 1 mmol), oxalyl chloride (420 μl) and catalytic amount of DMF in 5 ml DCM was stirred at r.t for 2 h before evaporation to dryness. The resulting solid residue was dissolved in 5 ml DCM and to which were added 2-chloroaniline (209 μl, 2 eq) and DIEA (522 μl). The reaction mixture was stirred at r.t for overnight before worked up with EA/aq. HCl/brine. The org. phase was concentrated and then purified on a flash silica gel column to give 291 mg (5-bromo(2-thienyl))-N-(2-chlorophenyl)carboxamide (7) as light yellow solid. (yield: 92%, purity>90%).

Provenance & Evidence