4-Nitrobenzaldehyde → HCID 23157603, compound

Participants

Reaction Steps

A suspension of ethyl bromodifluoroacetate (20.3 g, 100 mmol) and zinc powder (6.5 g, 100 mmol) in tetrahydrofuran (100 mL) was heated under reflux for 10 min, and 4-nitrobenzaldehyde (8.4 g, 55.8 mmol) was added dropwise. The reaction mixture was refluxed for 4 hr and allowed to cool to room temperature. Aqueous sodium hydrogensulfate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (4.80 g, yield 20%) as a yellow oil.

Provenance & Evidence