Hydrochloric Acid → (4-Methoxyphenyl)boronic acid

Participants

Reaction Steps

A solution of the Grignard reagent, prepared from 4-bromoanisole (80.0 g, 0.43 mol) and magnesium (11.96 g, 0.49 mol) in dry THF (300 ml) was added dropwise to a stirred, cooled (-78° C.) solution of tri-isopropyl borate (161.7 g, 0.86 mol) in dry THF (50 ml) under dry nitrogen. The stirred mixture was allowed to warm to room temperature overnight and was then stirred at room temperature for 1 h with 10% hydrochloric acid (300 ml). The product was extracted into ether (twice), the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a cream-coloured solid (58.5 g) which was recrystallised from water to give colourless crystals.

Provenance & Evidence