Hydrochloric Acid → 4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Participants

Reaction Steps

2.40 g (99.0 mmol) of magnesium and 25.56 g (89.6 mmol) of 4-octyloxybromobenzene in 250 ml of tetrahydrofuran are used to prepare, at 60° C. for 3 hours, the solution of the Grignard compound, which is added dropwise to a solution, cooled to -70° C., of 18.62 g (99.00 mmol) of triisopropyl borate in 100 ml of tetrahydrofuran, and the mixture is stirred overnight. 130 ml of 10% strength hydrochloric acid are subsequently added dropwise, the mixture is stirred at room temperature for 1 hour and partitioned between sodium chloride solution and ether, and the organic phase is washed with sodium chloride solution, dried over sodium sulfate and evaporated, giving 21.26 g of 4-octyloxybenzeneboronic acid. ##STR14##

Provenance & Evidence