Hydrochloric Acid → 4'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)

Participants

Reaction Conditions

Reaction Steps

4-Bromo-4′-pentylbiphenyl (3 g, 9.9 mmol) was added in one portion to Mg (0.27 g, 11.1 mmol), treated with I2, in THF (40 mL). The mixture was heated at reflux for 3 h, cooled to −78° C. and trimethyl borate (2.06 g, 19.8 mmol) was added dropwise. The mixture was warmed to room temperature over 1 h, acidified with HCl (2 M, 50 mL), extracted with Et2O (3×50 mL). The combined ethereal washes were extracted with NaOH (100 mL, 1 M). The aqueous phase was acidified with concentrated HCl, extracted with Et2O (3×50 mL), dried (MgSO4) and the solvent removed under reduced to give the title compound (2.07 g, 78%) as an off white powder.

Provenance & Evidence