Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

To a dimethylformamide (30 mL) solution of (4-bromophenyl)methanol (3.00 g), imidazole (2.18 g) and tert-butyldimethylsilyl chloride (2.89 g) were added in this order. The reaction solution was stirred at room temperature for one hour. To the reaction solution, water (10 mL) was added and the aqueous layer was extracted twice with ethyl acetate (50 mL). The combined organic layer was washed in turn with 1N hydrochloric acid (10 mL) and saturated sodium chloride solution (10 mL) and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→9:1) to obtain the title compound (3.77 g) having the following physical properties.

1. extractionthe aqueous layer was extracted twice with ethyl acetate (50 mL)
2. washThe combined organic layer was washed in turn with 1N hydrochloric acid (10 mL) and saturated sodium chloride solution (10 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. customAfter removing the anhydrous magnesium sulfate
5. filtrationby filtration
6. concentrationthe filtrate was concentrated
7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→9:1)

ORD record

ord-6a9da6caf2be40358a6768fe1f96d743

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871210B2