Thionyl Chloride → 1-Indanone, 6-bromo-

To a 250 mL of flask was added 3-(4-bromo-phenyl)-propionic acid 38a (20.6 g, 90 mmol, ABCR) and dried in vacuo for 20 minutes followed by addition of 110 mL of anhydrous dichloromethane under nitrogen atmosphere, and then thionyl chloride (20 mL, 276 mmol) was added. The reaction mixture was heated to reflux overnight. The mixture was concentrated under reduced pressure to remove most solvent followed by addition of 100 mL of dichloromethane, and then aluminium trichloride (24.5 g, 25.8 mmol) was added. The generated gas was released. The mixture was warmed up to reflux and stirred overnight. The mixture was poured into 200 g of ice to form a copious amount of precipitates and filtered through silica gel. The filtrate was separated and the aqueous layer was extracted with 30 mL of dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound 6-bromo-indan-1-one 38b (18.34 g, yield 96.6%) as a yellow solid.

1. customdried in vacuo for 20 minutes
2. additionfollowed by addition of 110 mL of anhydrous dichloromethane under nitrogen atmosphere
3. temperatureThe reaction mixture was heated
4. temperatureto reflux overnight
5. concentrationThe mixture was concentrated under reduced pressure
6. customto remove most solvent
7. additionfollowed by addition of 100 mL of dichloromethane
8. temperatureThe mixture was warmed up
9. temperatureto reflux
10. customto form a copious amount
11. customof precipitates
12. filtrationfiltered through silica gel
13. customThe filtrate was separated
14. extractionthe aqueous layer was extracted with 30 mL of dichloromethane
15. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
16. concentrationconcentrated under reduced pressure

ORD record

ord-99a246c310af41a79af491178b725068

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2