Thionyl Chloride → 1-Indanone, 6-bromo-

Thionyl chloride (15.6 g, 131.1 mmol) was added slowly to a solution of 3-(4-bromo-phenyl)-propionic acid (available from Transworld Chemicals, 10.0 g, 43.7 mmol) in 100 mL of dichloromethane at room temperature. The mixture was then heated at reflux for 14 h. After cooling to room temperature, the solvent and excess thionyl chloride were removed under reduced pressure to afford a yellow crude oil. The crude product was then dissolved in 100 mL of dichloromethane and aluminum chloride (17.5 g, 131.1 mmol) was added portionwise at room temperature. After heating at reflux for 5 h, the mixture was then slowly poured into ice-water, extracted with dichloromethane (3×50 mL), washed with brine (1×50 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (95:5 hexane/ethyl acetate) yielded the title compound (8.94 g, 97% yield) as a light yellow solid:

1. temperatureThe mixture was then heated
2. temperatureat reflux for 14 h
3. customthe solvent and excess thionyl chloride were removed under reduced pressure
4. customto afford a yellow crude oil
5. temperatureAfter heating
6. temperatureat reflux for 5 h
7. extractionextracted with dichloromethane (3×50 mL)
8. washwashed with brine (1×50 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated at reduced pressure
11. customPurification by flash chromatography (95:5 hexane/ethyl acetate)

ORD record

ord-bef03b09081243799d9817103b3448c0

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253319B2