Description
4-(Morpholinomethyl)phenylboronic acid is a synthetic intermediate compound that serves in the preparation of pharmaceuticals, plastics, pesticides and herbicides. This compound combines the reactivity of the boronic acid group with the polar characteristics of the morpholine group, which helps to form stable compounds whilst improving drug solubility.
Synthesis
A) General procedure for the synthesis of 4-morpholinomethylphenylboronic acid: morpholine (0.304 mL) was added to a solution of acetonitrile (10 mL) containing 4-(bromomethyl)phenylboronic acid (500 mg) and potassium carbonate (643 mg). The reaction mixture was stirred at room temperature for 60 hours. Upon completion of the reaction, water was added to the mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine and subsequently dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was washed with diisopropyl ether and ethyl acetate to give the final 4-morpholinomethylphenylboronic acid (449 mg). Mass spectrometry analysis (ESI+): [M + H]+ calculated value 222.1, measured value 222.2.
References
[1] Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 3 - 15
[2] Patent: WO2004/81008, 2004, A1. Location in patent: Page 101-102
[3] Patent: EP2857400, 2015, A1. Location in patent: Paragraph 0843
[4] Patent: WO2017/137535, 2017, A1. Location in patent: Page/Page column 129
[5] Dyes and Pigments, 2018, vol. 149, p. 356 - 362
