Thionyl Chloride → 5-Bromo-6-methoxy-1-indanone

Participants

Reaction Steps

3-(3-Bromo-4-methoxyphenyl)propionic acid (5.0 g, 19.3 mmol) and thionyl chloride (10 ml) were refluxed for 1 hour. This reaction mixture was concentrated under reduced pressure to remove the excess thionyl chloride and the residue was dissolved in 1,2-dichloroethane (50 ml). To this solution was added aluminum chloride (2.8 g, 20.8 mmol) over 10 minutes on an ice bath and the mixture was further stirred at room temperature for 1 hour. This reaction mixture was poured in iced water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane to provide the title compound (yield 4.3 g, 92%).

Provenance & Evidence