N-bromobutanimide → Methyl 2-bromo-5-phenylthiophene-3-carboxylate

Participants

Reaction Steps

N-Bromosuccinimide (360 mg, 2.02 mmol) was added to a solution of methyl 5-phenylthiophene-3-carboxylate (11b) (440 mg, 2.02 mmol) in a mixture of N,N-dimethylformamide (4 mL) and tetrahydrofuran (4 mL). The reaction mixture was stirred at room temperature for 1 hour. N-Bromosuccinimide (72 mg, 0.40 mmol) was added and the stirring was maintained for 1 hour. The mixture was poured in water (10 mL) and extracted with dichloromethane (2×15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to provide the desired product (11c) (390 mg, 1.3 mmol, 65%).

Provenance & Evidence