2,6-Lutidine → 2-Bromo-1-(5-methylpyrazin-2-yl)ethanone

Participants

Reaction Steps

To a chloroform (28 mL) solution of 1-(5-methylpyrazin-2-yl)ethanone (1.9 g), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (2.7 mL) and trimethylsilyl trifluoromethanesulfonate (3.0 mL) were added, and the resultant was stirred for 30 minutes. Then, N-bromosuccinimide (3.0 g) was added thereto, and the resultant was stirred at room temperature for 1 hour. Water was added to the reaction solution, and the resultant was stirred for 15 minutes, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=90/10→60/40) and then further purified by hexane/ethyl acetate-gradient elution (=90/10→80/20) to obtain the title compound (2.1 g) as a pale yellow solid.

Provenance & Evidence