Hydrochloric Acid → p-Chlorophenylboric acid

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-bromophenyl (70.6 g) was dissolved in a mixture of toluene (588.3 ml) and THF (147 ml) under argon, and n-BuLi (176.4 ml, 2.5M in hexane) was added dropwise at −78° C., stirred for 1 hours, then tri-isopropyl borate (109.2 ml) was added dropwise at −78° C., stirred for 1 hour. HCl (360.4 ml, 2.2 mol/l) was added at −20° C., and warmed to 110° C., the reaction was diluted with water, the aqueous layer was extracted with toluene (35 ml, twice). The extract and the organic layer were washed with saturated brine, dried over anhydrous Na2SO4 over night. The organic layer was concentrated under reduced pressure to give 4-chlorophenylboric acid (48 g) as a solid after crystallization (toluene).

Provenance & Evidence