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

Participants

Reaction Steps

n-Butyllithium (23 ml, 2.5M in hexane, 0.058 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 26 (15.00 g, 0.053 mol) in dry THF (168 ml) under dry nitrogen. The reaction mixture was maintained under these conditions for 2.5 h and then a solution of trimethyl borate (10.98 g, 0.106 mol) in dry THF (50 ml) was added dropwise at -78° C. The reaction mixture was allowed to warm to room temperature overnight and then stirred for 1 h with 10% hydrochloric acid (120 ml). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield an off white solid.

Provenance & Evidence