Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

A solution of 11.5 g (66.5 mmol, Aldrich) of m-bromophenol, 6.80 g (100 mmol, Aldrich) of imidazole and 10.3 g (68.3 mmol, Aldrich) of chloro-t-butyldimethylsilane in 75 mL of sieve-dried dimethylformamide was stirred at room temperature for 18 hours. The reaction mixture was then partitioned between 250 mL of cold 1M aqueous HCl solution and 150 mL of hexane. The organic layer was separated and the aqueous layer extracted with an additional 100 mL of hexane. The organic extracts were combined, washed with 100 mL of saturated aqueous sodium bicarbonate solution, then 100 mL of water, dried (magnesium sulfate) and concentrated in vacuo to afford 18.8 g (65.5 mmol, 99%) of title compound as a colorless oil.

1. customThe reaction mixture was then partitioned between 250 mL of cold 1M aqueous HCl solution and 150 mL of hexane
2. customThe organic layer was separated
3. extractionthe aqueous layer extracted with an additional 100 mL of hexane
4. washwashed with 100 mL of saturated aqueous sodium bicarbonate solution
5. dry with material100 mL of water, dried (magnesium sulfate)
6. concentrationconcentrated in vacuo

ORD record

ord-1c60f807efe14d79a617f69cb2c5d0cb

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04883809