Triisopropyl borate → HCID 58452416, compound

Temperature

-78 °C

A solution of 4-bromo-2-methylbenzotrifluoride (500 mg) in tetrahydrofuran (5 mL) was cooled to an external temperature of −78° C. in a nitrogen atmosphere, and a solution of n-butyllithium in hexane (1.57 M, 2.0 mL) was added dropwise. After stirring at −78° C. for 30 minutes, triisopropyl borate (0.72 mL) was added dropwise and the mixture was stirred at room temperature overnight. Acetic acid (0.18 mL) and 2,2-dimethyl-1,3-propanediol (240 mg) were added, followed by stirring at room temperature for three hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give the title compound as a colorless solid (353 mg, 62%).

1. stirringthe mixture was stirred at room temperature overnight
2. stirringby stirring at room temperature for three hours
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customThe solvent was then evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

ORD record

ord-ec6f6bd6a9e147a183342d269e4649d6

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822503B2