Tetrahydrofuran → 4-Bromo-2-nitrobenzaldehyde

Participants

Reaction Steps

To a solution of crude (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethenamine (35.5 g, 131 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (56.0 g, 262 mmol). The solids were removed and the filter cake was washed with EtOAc (200 mL). The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (5% EtOAc/hexanes to 10% EtOAc/hexanes) to provide 4-bromo-2-nitrobenzaldehyde (8.41 g, 28% yield).

Provenance & Evidence