Triethylsilane → 5-Bromo-2,2-dimethyl-2,3-dihydro-1H-indene

6-Bromo-2,2-dimethyl-indan-1-one 45a (7.23 g, 30.3 mmol) was dissolved in 150 mL of trifluoroacetic acid followed by addition of triethylsilane (12.1 mL, 75.6 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials and then quenched by addition of water. The mixture was concentrated under reduced pressure to remove trifluoroacetic acid. The mixture was adjusted to be basic with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate (50 mL×3). The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 5-bromo-2,2-dimethyl-indan 45b (14 g) as a colourless oil, which was directly used in the next step.

1. customquenched by addition of water
2. concentrationThe mixture was concentrated under reduced pressure
3. customto remove trifluoroacetic acid
4. extractionextracted with ethyl acetate (50 mL×3)
5. washThe combined organic extracts were washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customto remove the drying agent
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-733bb4b8f8bd4bf99c3d20d24ccdc63a

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2