Triisopropyl borate → 4-Fluoro-3-(hydroxymethyl)benzeneboronic acid

Participants

Reaction Conditions

Reaction Steps

To solution of (5-bromo-2-fluoro-phenyl)-methanol (1.0 eq) in THF (0.1M) at −78° C. was added dropwise n-BuLi (2.5M in Hex; 2.2 eq). The resulting mixture was stirred at −78° C. for 30 min then tri-isopropoxy borane (2.2 eq) was added. The final mixture was stirred 15 min at −78° C. then allowed to warm slowly to room temperature and stirred an extra hour. The reaction was quenched with HCl (10%) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in EtOAc, water (few drops) was added then hexane until a precipitate formed. After 12 h of stirring, the desired compound was isolated by filtration as a white solid.

Provenance & Evidence