Chlorotrimethylsilane → HCID 66965226, compound

Temperature

0 °C

To a solution of diisopropylamine (15.5 mL, 110 mmol) in THF (100 mL) at 0° C. was added n-butyllithium (40 mL of 2.5M in hexanes, 100 mmol). The resultant reaction solution was stirred at 0° C. for 30 minutes and then cooled to −40° C., before it was cannulated to a solution of 5-bromobenzothiophene (10.5 g, 50.0 mmol) and chlorotrimethylsilane (12.7 mL, 100 mmol) in THF (150 mL) at −78° C. The reaction solution was stirred at −78° C. for 1 hour, and then it was quenched with aqueous ammonium chloride at −78° C. and warmed to room temperature. The resultant mixture was extracted with ethyl acetate and the organic extract obtained was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by flash column chromatography (hexanes to 98:2 hexanes/ethyl acetate) to give the desired 5-bromo-2-trimethylsilylbenzothiophene (14.1 g, 98%) as a clear colorless oil: 1H NMR (500 MHz, CDCl3) δ 7.93 (d, J=2.0 Hz, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.39 (dd, J=8.5, 2.0 Hz, 1H), 7.37 (s, 1H), 0.38 (s, 9H).

1. customThe resultant reaction solution
2. temperaturecooled to −40° C., before it
3. stirringThe reaction solution was stirred at −78° C. for 1 hour
4. customit was quenched with aqueous ammonium chloride at −78° C.
5. temperaturewarmed to room temperature
6. extractionThe resultant mixture was extracted with ethyl acetate
7. extractionthe organic extract
8. customobtained
9. washwas washed with brine
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated in vacuo
12. customThe residue obtained
13. customwas purified by flash column chromatography (hexanes to 98:2 hexanes/ethyl acetate)

ORD record

ord-44fc35cd29244c75ad625f25c139e89c

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403776B2