Triisopropyl borate → 2-(2-Methoxyethyl)phenylboronic acid

Temperature

-78 °C

To a solution of 2-(2-bromophenyl)ethyl methyl ether (V.2; 1 eq.) in THF (0.16M) at −78° C. was added n-butyllithium (2.5M; 1.1 eq.). The reaction mixture was stirred for 1 h at −78° C. then tri-iso-propylborate (1.2 eq.) was added and the final mixture was allowed to warm slowly to room temperature and stirred for 1 h. The reaction was quenched with the addition of aqueous HCl (1N) and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated to afford the desired material as a foam which was used as such.

1. temperatureto warm slowly to room temperature
2. stirringstirred for 1 h
3. customThe reaction was quenched with the addition of aqueous HCl (1N)
4. extractionextracted with EtOAc
5. extractionThe organic extract
6. washwas washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-db85cea7e1664d38b59e2ba904e6f4d2

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334308B2