Hydrochloric Acid → 1-Indanone, 6-bromo-

3-(4-Bromophenyl)propionic acid (162 g, 706 mmol) and thionyl chloride (155 mL, 2120 mmol) were refluxed for 90 minutes. The thionyl chloride was then removed under vacuum to yield an amber oil. This oil, aluminum chloride (109 g, 816 mmol), and dichloromethane (1000 mL) were refluxed for 90 minutes and then poured onto ice. Dilute hydrochloric acid was added and the mixture was extracted with diethyl ether. The organic layer was washed with 2N hydrochloric acid, water, aqueous sodium bicarbonate, water, and brine. The product was flash chromatographed on a 25×7 cm silica gel column and eluted with ethyl acetate/dichloromethane (5:95) to obtain a pale brown solid after removing solvent under vacuum, (142 g, 95%), 107-109° C. m.p.

1. customThe thionyl chloride was then removed under vacuum
2. customto yield an amber oil
3. additionpoured onto ice
4. extractionthe mixture was extracted with diethyl ether
5. washThe organic layer was washed with 2N hydrochloric acid, water, aqueous sodium bicarbonate, water, and brine
6. customchromatographed on a 25×7 cm silica gel column
7. washeluted with ethyl acetate/dichloromethane (5:95)
8. customto obtain a pale brown solid
9. customafter removing solvent under vacuum, (142 g, 95%), 107-109° C. m.p.

ORD record

ord-3d0ab8e621b640a2bc6c9563500cf84b

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05936000