Ethylene → HCID 11953413, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL Parr reactor Model # 4768 was added 4.6 g, 20 mmol of 5bromo-2-nitrobenzaldehyde of example 1 with dimethylformamide (30 mL), triethylamine (9.1 g, 90 mmol), tri-o-tolyl phosphine (0.060 g, 0.2 mmol), and palladium acetate (0.022 mg, 0.1 mmol). The reactor was charged with ethylene gas (300 psi) and heated to 100° C. for 12 hours. The reactor was then cooled to room temperature and the excess ethylene released. The product, 5-vinyl-2-nitrobenzaldehyde, was recovered by dissolving the reaction mixture in water and washing the aqueous solution with ether (3×50 mL). The combined organic solutions were dried over magnesium sulfate before filtration, followed by removal of the solvent by vacuum. The 5-vinyl-2-nitrobenzaldehyde product was purified by column chromatography with silica gel as stationary phase and chloroform as eluent to give a light brown solid (1.9 g, 53% yield).

Provenance & Evidence