Triisopropyl borate → 2-Methoxy-5-(trifluoromethyl)phenylboronic acid

Temperatur

-78 °C

n-Butyl lithium (1.6M in hexanes, 456 μL, 0.729 mmol) was added dropwise to a stirred solution of 2-iodo-1-methoxy-4-(trifluoromethyl)benzene (Step A, 200 mg, 0.662 mmol) in THF (1.5 mL) at −78° C. under an atmosphere of nitrogen. The reaction stirred at −78° C. for 30 min prior to the addition of triisopropyl borate (458 μL, 1.986 mmol). The reaction stirred an additional 2 h at −78° C. and was quenched with sat. NH4Cl. The mixture was extracted with CH2Cl2 and the organic phase was washed with NaHCO3 (15 mL) and brine (15 mL), dried (Na2SO4), filtered, conc. in vacuo to afford [2-methoxy-5-(trifluoromethyl)phenyl]boronic acid which was carried on without purification.

1. stirringThe reaction stirred an additional 2 h at −78° C.
2. customwas quenched with sat. NH4Cl
3. extractionThe mixture was extracted with CH2Cl2
4. washthe organic phase was washed with NaHCO3 (15 mL) and brine (15 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered, conc. in vacuo

ORD-Eintrag

ord-3cd4d6b95d6541fdb506a31e7bbe2ed8

Quelldatensatz

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08735435B2