Hydrochloric Acid → p-Chlorophenylboric acid

Temperature

110 °C

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).

1. stirringstirred for 1 hour
2. extractionthe aqueous layer was extracted with toluene (35 ml
3. extractionThe extract
4. washthe organic layer were washed with saturated brine
5. dry with materialdried over anhydrous Na2SO4 over night
6. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-77adbc5f232149c883362bbdcf988f45

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318740B2