Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

Temperature

0 °C

Combine imidazole (59.9 g, 880 mmol), t-butyldimethylsilyl chloride (60.3 g, 400 mmol), and dimethylformamide (300 mL). Cool to 0° C. in a salt-ice bath. Add dropwise 2-bromoethanol (50.0 g, 400 mmol) at such a rate that the temperature of the reaction mixture does not rise above 0° C. After 2 hours, warm to ambient temperature. After 18 hours, extract the reaction mixture three times with hexane. Combine the hexane layers and extract three times with a saturated aqueous solution of ammonium chloride, three times with a saturated aqueous solution of sodium bicarbonate, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

1. customdoes not rise above 0° C
2. temperaturewarm to ambient temperature
3. waitAfter 18 hours
4. extractionextract the reaction mixture three times with hexane
5. extractionextract three times with a saturated aqueous solution of ammonium chloride, three times with a saturated aqueous solution of sodium bicarbonate
6. dry with materialDry the organic layer over Na2SO4
7. filtrationfilter
8. customevaporate in vacuo

ORD record

ord-cf86489096b248f0b5ba555f069230f3

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998439