Isobutyronitrile → 3-(2-Bromo-5-((tert-butyl(dimethyl)silyl)oxy)phenyl)-2,2-dimethylpropanenitrile

Under a nitrogen atmosphere, to a solution of diisopropylamine (0.70 mL) in THF (15 mL) was added a 1.6 M solution of n-butyllithium in hexane (3.0 mL) at 0° C., and the mixture was stirred for 10 min. Isobutyronitrile (0.47 mL) was added at −78° C., and the mixture was stirred for 30 min. A solution of (4-bromo-3-(bromomethyl)phenoxy) (tert-butyl)dimethylsilane (1.00 g) in THF (5.0 mL) was added, and the mixture was stirred at −78° C. for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (905 mg) as a colorless oil.

1. stirringthe mixture was stirred for 30 min
2. stirringthe mixture was stirred at −78° C. for 2 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-d91cb012c3f64ed79c18d91be5ed1ee9

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382188B2