N-bromobutanimide → Methyl 6-bromo-7-fluoro-chromane-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (336 mg, 1.60 mmol) was diluted with DMF (5 mL) followed by the addition of N-bromosuccinimide (313 mg, 1.76 mmol). The reaction was heated at 50° C. and stirred for 2.5 hours. The reaction was cooled, diluted with ethyl acetate and washed with water, saturated sodium bicarbonate, water, and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The material was purified by silica gel chromatography using a Biotage 40M cartridge (gradient 5% ethyl acetate/hexane) to 50% to yield the title compound (415 mg, 89.8% yield).

Provenance & Evidence