Sodium Chloride → 5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

Temperature

180 °C

1-(4-Bromo-2-fluoro-phenyl)-3-chloro-propan-1-one (27.45 g, 103 mmol) was added to a slurry of aluminum chloride (164 g, 1.23 mol) and sodium chloride (43.19 g, 0.739 mol) at 130° C. The mixture was stirred with a mechanical stirrer and heated to 180° C. for 6 hours. The whole mixture was quenched with ice and concentrated hydrochloric solution (122 ml, 1.24 mol). The resulting mixture was extracted with dichloromethane. The organic phase was washed with water, saturated sodium bicarbonate solution and brine, dried over sodium sulfate and filtered. After concentrating under reduced pressure, purification by silica gel chromatography afforded 5-Bromo-7-fluoro-indan-1-one (5 g, 21.8 mmol).

1. customThe whole mixture was quenched with ice
2. extractionThe resulting mixture was extracted with dichloromethane
3. washThe organic phase was washed with water, saturated sodium bicarbonate solution and brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationAfter concentrating under reduced pressure, purification by silica gel chromatography

ORD record

ord-b729298908ed4244b8d013547a32bb46

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299077B2