1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one → 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

Bromoacetyl bromide (1.0 mL, 11.2 mmol) was slowly added to a suspension of aluminum chloride (3.7 g, 27.9 mmol) in dichloromethane (30 mL) and the reaction mixture was stirred for 20 min at rt. A solution of 1-acetylindoline (1.5 g, 9.3 mmol) in dichloromethane (10 mL) was slowly added and then the reaction mixture was heated at 55° C. for 1.5 h. The mixture was cooled and then quenched with cold water. The precipitate was filtered through a short pad of celite, washed with dichloromethane and water. The aqueous phase was extracted with dichloromethane. The combined organic extract was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give the product. Yield: 1.9 g (73%).

1. temperaturethe reaction mixture was heated at 55° C. for 1.5 h
2. temperatureThe mixture was cooled
3. customquenched with cold water
4. filtrationThe precipitate was filtered through a short pad of celite
5. washwashed with dichloromethane and water
6. extractionThe aqueous phase was extracted with dichloromethane
7. extractionThe combined organic extract
8. washwas washed with brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customto give the product

ORD record

ord-79502e5172db494b984fb6a4dae067cb

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859534B2