Trimethyl borate → 5-(tert-Butyl)-2-methoxybenzeneboronic acid

Temperature

-78 °C

To a solution of 4-tert-butyl-2-iodo-1-methoxybenzene (0.164 g, 0.56 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.27 mL, 0.68 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.19 mL, 1.70 mmol) was added. The solution was stirred at −78° C. for 3 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent.

1. stirringThe solution was stirred at −78° C. for 3 h
2. customThe reaction was quenched with saturated aqueous NH4Cl
3. extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
4. dry with materialThe combined EtOAc layers were dried over Na2SO4
5. customThe residue was used without further purification
6. customafter evaporation of the solvent

ORD record

ord-dfe5c271b00d45bc8ac467ae3c6fd1e8

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910592B2