2-Phenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Synthesis

98-80-6

4408-64-4

109674-45-5

The general procedure for the synthesis of MIDA ester of phenylboronic acid from phenylboronic acid and N-methyliminodiacetic acid (MIDA) was as follows: phenylboronic acid (0.98 kg, 8 mol) and N-methyliminodiacetic acid (MIDA) (1.3 kg, 9 mol) were homogeneously dispersed in a solvent mixture of toluene (90 L) and dimethylsulfoxide (10 L) (the volume ratio of toluene to dimethyl sulfoxide was 9:1). (the ratio of toluene to dimethyl sulfoxide was 9:1). The reaction was refluxed at 120 °C for 4 h. After completion of the reaction, it was slowly cooled to room temperature. Toluene was removed by rotary evaporation and the residue was diluted with water. The aqueous phase was extracted three times using an appropriate amount of ethyl acetate, the organic phases were combined and washed three times with saturated saline. The organic phase was collected, dried by adding anhydrous magnesium sulfate, filtered and the ethyl acetate was removed by rotary evaporation. The crude product was recrystallized in petroleum ether, filtered to give a light yellow solid product and finally dried under vacuum overnight.