Triisopropyl borate → 4-(2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy)-3-(trifluoromethyl)phenylboronic acid

温度

-78 °C

BuLi (2.5M, 6 ml) was added dropwise to a solution of 2-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethoxy)tetrahydro-2H-pyran (5 g) in THF (50 ml) at −78° C. under N2 during 3 minutes. After stirring at −78° C. for another 10 minutes, triisopropyl borate (3.8 ml) was then added dropwise during 2 minutes at −78° C. The mixture was stirred at −78° C. for further 30 minutes, then slowly warmed up to room temperature and stirred at room temperature for 30 minutes. The mixture was then quenched with acetic acid (10% in water, 20 ml), extracted with EtOAc (300 ml), washed with water (200 ml×3), dried over sodium sulphate, solvent removed under reduced pressure, the residue was taken in to toluene and then solvent removed under reduced pressure to take out traces of acetic acid (repeat 3 times) (4.5 g).

1. stirringThe mixture was stirred at −78° C. for further 30 minutes
2. temperatureslowly warmed up to room temperature
3. stirringstirred at room temperature for 30 minutes
4. customThe mixture was then quenched with acetic acid (10% in water, 20 ml)
5. extractionextracted with EtOAc (300 ml)
6. washwashed with water (200 ml×3)
7. dry with materialdried over sodium sulphate, solvent
8. customremoved under reduced pressure
9. customsolvent removed under reduced pressure

ORDレコード

ord-3f55f8954af14e8a98c6957c10ce4b39

出典データセット

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08026236B2