Methanol → 5-Bromo-3-fluoro-2-nitroanisole

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-1,3-difluoro-2-nitrobenzene (Compound 146H, 2.00 g, 8.40 mmol) in MeOH (15.0 mL) was added potassium hydroxide (504 mg, 8.98 mmol). The reaction was stirred at 90° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (15 mL), washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a yellow solid. The crude material was purified by silica gel chromatography on an ISCO combi-flash Rf system using Heptane/EtOAc (100:0→70:30) as eluent to yield the desired product as a light yellow solid 1.75 g (83% yield). 1H NMR (CDCl3, 400 MHz): δ=3.95 (s, 3H), 7.01 (s, 1H), 7.05 (dd, J=8.59, 1.77 Hz, 1H).

Provenance & Evidence