Hydrochloric Acid → 3,5-Dichlorophenylboronic acid

Participants

Reaction Conditions

Reaction Steps

To a cold (-78° C.) solution of 1-bromo-3,5-dichlorobenzene (14 g) and triisopropoxyborane (20.8 ml) in tetrahydrofuran (140 ml) was added dropwise n-butyllithium in hexane (1.66 M, 52.3 ml). The mixture was stirred at -78° C. for one hour and warmed to room temperature over two hours. The reaction mixture was poured onto 2M hydrochloric acid solution (120 ml) and stirred for 10 minutes. The product was extracted with ether (200 ml) 3 times, and the organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated in vacuo. To the residue was added petroleum ether and the crystalline was collected, washed with petroleum ether and dried to give 3,5-dichlorophenyl-dihydroxyborane.

Provenance & Evidence