4-(4-Nitrophenyl)butanal → 1,2-Dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzene

Participants

Reaction Conditions

Reaction Steps

A solution of bromo[(3,4-dichlorophenyl)methyl]triphenylphosphine (3.95 g, 7.9 mmol) in dry THF (20 mL) was cooled to 0° C. LHDMS (1.0 M/THF, 9 ml, 9.0 mol) was added dropwise to maintain the temperature at 0° C. After stirring for 30 minutes, a solution of 4-(4-nitro-phenyl)butyraldehyde (1.45 g, 7.5 mmol) in TBF (5 mL) was added dropwise, and the mixture was allowed to warm to room temperature within 2 hours. The mixture was then quenched with H2O and extracted with EtOAc. The organic layers were washed with 0.1N HCl solution, H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a lightly brown oil. Purification by flash chromatography (silica gel, 10% EtOAc/hexane) yielded 2.5 g (7.4 mmol, 99%) of the desired product.

Provenance & Evidence