Methanol → 4-Bromo-5-fluoro-2-nitrobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-bromo-5-fluoro-2-nitrobenzoate (5.348 g, 19.24 mmol) in DCM (100 mL) at −78° C., a solution of diisobutylaluminum hydride in DCM (1.0 M, 25.0 mL, 25.0 mmol) was added dropwise over a period of 10 min. The mixture was stirred at −78° C. for 2 h. MeOH (10.0 mL) was then added. The reaction mixture was allowed to warm to room temperature. A 10 wt % aqueous solution of sodium tartrate (100 mL) was added to the mixture. The mixture was then stirred vigorously until a distinct bilayer was formed. The mixture was then diluted with DCM (100 mL), washed with water (2×100 mL), brine (2×100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-30% EtOAc in Hexanes) to give the sub-title compound as a pale yellow solid (4.19 g, 88%). LCMS calc. for C7H4BrFNO3 (M+H)+: m/z=247.9; found no ionization.

Provenance & Evidence