Chemical Properties
White to light yellow crystal powde
Uses
4-(Methoxycarbonyl)phenylboronic Acid is a reagent used for• ;Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence1 • ;Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2 • ;One-pot ipso-nitration of arylboronic acids3 • ;Copper-catalyzed nitration4 • ;Cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling5 • ;Reagent used in Preparation of• ;Biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6† • ;Chromenones and their
Uses
4-(Methoxycarbonyl)phenylboronic Acid is used in the synthesis and evaluation of several organic compounds including that of 4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate which is a potent inhibitor of intracellular NAAA activity. Also used in the design and synthesis of BMS-955176 which is a potent, orally active second generation HIV-1 maturation inhibitor.
Synthesis
In a 500 mL three-neck flask, methyl 4-bromobenzoate (20.2 g, 77.2 mmol) was dissolved in anhydrous THF (200.0 mL) and triisopropyl borate (18.9 g, 100.3 mmol) was added. The reaction mixture was cooled to -78 °C, N-butyllithium (6.8 g, 96.5 mmol) was slowly added dropwise and the reaction was kept at this temperature for 0.5 h. The reaction was completed with the addition of saturated chloride (1.2 mmol). Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution, followed by adjusting the pH with 1 mol/L hydrochloric acid to 1. The aqueous phase was extracted with ethyl acetate (100.0 mL x 3), the organic phases were combined, washed with saturated brine (60 mL x 1) and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, the residue was pulped with hexane, and 13.3 g of 4-methoxycarbonylphenylboronic acid was obtained after filtration in 95.5% yield.
References
[1] Patent: CN106565761, 2017, A. Location in patent: Paragraph 0063; 0064
