Triethylsilane → 5-bromo-2,3-dihydro-1H-indene

A solution of 5-bromo-2,3-dihydro-1H-inden-1-one (4.74 mmol) in HF-pyridine (5 mL) in a 100 mL Nalgene round bottomed flask was cooled to 0° C. and treated with triethylsilane (11.85 mmol) over a period of 5 min. The reaction solution was allowed to warm to room temperature and was stirred for 3 h. Analysis by LCMS indicated only partial conversion of the starting material, so the reaction contents were cooled to 0° C. and treated with more triethylsilane (11.85 mmol). The reaction solution was allowed to warm to room temperature and was stirred for 2 days. The reaction was quenched with 50 mL of ice water and after one hour was further diluted with an additional 50 mL of water. The mixture was extracted with dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexanes) to afford the title compound as a clear oil (65%). 1H NMR (400 MHz, CDCl3) δ ppm 7.35 (s, 1H) 7.23 (d, J=2.02 Hz, 1H) 7.08 (d, J=8.08 Hz, 1H) 2.79-2.96 (m, 4H) 2.05-2.11 (m, 2H).

1. customso the reaction contents
2. temperaturewere cooled to 0° C.
3. temperatureto warm to room temperature
4. stirringwas stirred for 2 days
5. customThe reaction was quenched with 50 mL of ice water and after one hour
6. additionwas further diluted with an additional 50 mL of water
7. extractionThe mixture was extracted with dichloromethane
8. dry with materialThe resulting organic layer was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe resulting residue was purified by silica gel chromatography (hexanes)

ORD record

ord-d55cdfb2c6714fdfb48eb870949b9965

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802864B2