Triisopropyl borate → (3-Chloro-2-methylphenyl)boronic acid

To a solution of 10.0 g (48.7 mmol) 2-bromo-6-chlorotoluene and 11.3 ml (48.7 mmol) triisopropyl borate in 90 ml dry THF were added dropwise 30 ml (49 mmol) of a 1.6 M solution on n-butyllithium in hexanes at −78° C. under argon. After 45 min the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 5 ml water and the solvent was evaporated in vacuo. Addition of 1 M aqueous hydrochloric acid solution was followed by extraction with four portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Crystallisation from heptane gave 5.08 g (61%) of the title compound as a white solid.

1. customThe reaction was quenched by addition of 5 ml water
2. customthe solvent was evaporated in vacuo
3. additionAddition of 1 M aqueous hydrochloric acid solution
4. extractionwas followed by extraction with four portions of dichloromethane
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customCrystallisation from heptane

ORD record

ord-891a7d020c434cae997ef59cdc3de24e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404708B2