Chemical Properties
White to light yellow crystal powde
Uses
Reagent used for tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, one-pot ipso-nitration of arylboronic acids, copper-catalyzed nitration, cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling. Reagent used in Preparation of biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6, chromenones and their bradykinin B1 antagonistic active, Pt nanoparticles at Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injecti, salicylate-based thienylbenzoic acids as E. coli methionine aminopeptidase inhibitor.
Uses
3-Methoxycarbonylphenylboronic acid can be used in the preparation of substituted pyrazolylpyrimidinamine derivative for use as protein kinase inhibitors and suzuki reaction.
Synthesis
In a 20 L reactor, 8.0 Kg of anhydrous methanol and 1.66 Kg (10 mol) of 3-carboxyphenylboronic acid were added and stirring was initiated. The reaction mixture was heated to 55°C and the temperature was maintained in the range of 55-65°C. 1.78Kg (15mol) of thionyl chloride was slowly added dropwise to the reaction kettle. After completion of the reaction, reflux was continued for 2-3 hours. The completion of the reaction was confirmed by TLC (unfolding agent: n-heptane/ethyl acetate = 2:1). The reaction solution was then cooled and subjected to reduced pressure distillation to remove the solvent. N-heptane was added and the mixture was cooled to -10 to 0°C and filtered with continuous stirring for 1 hour. The solid product was collected and dried at 80 °C until the absence of impurities was confirmed by HNMR (DMSO-d6, δ=3.16 ppm). The dried solid was stirred at room temperature and water was added, filtered and dried at room temperature to give 1.75 Kg of the final white solid product m-Carbomethoxyphenylboronic acid in 97.1% yield.
References
[1] Patent: CN106188117, 2016, A. Location in patent: Paragraph 0015
