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

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%).

1. concentrationThis reaction mixture was concentrated under reduced pressure
2. customto remove the excess thionyl chloride
3. dissolutionthe residue was dissolved in 1,2-dichloroethane (50 ml)
4. extractionextracted with ethyl acetate
5. washThe extract was washed serially with saturated saline and water
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. washThe residue was washed with hexane

ORD-Eintrag

ord-9e18e03211e549bea746cb71efffd8d5

Quelldatensatz

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05922771