Carbon tetrabromide → HCID 16107231, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-formyl-4-nitrobenzoate (23.7 mmol) and carbontetrabromide (8.66 g, 26.1 mmol) in dichloromethane (50 ml) was added dropwise a solution of triphenylphosphine (12.44 g, 47.5 mmol) in dichloromethane (50 ml) at 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h at 0° C. and then allowed to warm to room temperature. A small amount of white solid was formed. The solution was concentrated to 30 mL and then filtered. The organic solvent was concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, 10% EtOAc in hexanes as eluent) to afford methyl 3-(2,2-dibromovinyl)-4-nitrobenzoate was obtained as a light tan solid (32 g, 74%); 400 M Hz 1H NMR (CDCl3) 8.26 (br s, 1H), 8.12-8.18 (m, 2H), 7.75 (s, 1H), 3.98 (s, 3H).

Provenance & Evidence