preparation | adding pinacol borate (8.6g,31.4 mmol),PdCl2(PPh3)2(0.42mmol) and KOAc(94.2mmol) to dioxane (154 mL) solution of methyl 2-chloro-4-bromobenzoate (31.4 mmol), stirring the mixture at 100 ℃ under nitrogen for 2-6 hours. Dilute the mixture with EtOAc and water. The organic layers were separated, washed with brine, dried by MgSO4, and evaporated. The residue was purified by silica gel column chromatography (hexane/EtOAc 5/1) to give 3-chloro-4-methoxycarbonylphenylboronic acid pinacol ester. NH4OAc(66.2mmol) and NaIO4(14.2g,66.4mmol) were added to the suspension of the above product (29.4mmol) in acetone (175mL) and water (175mL), and the mixture was stirred at room temperature for 15 hours. The solvent was evaporated and the residue was diluted with EtOAc. The organic layer was separated, washed with water and salt water, dried by MgSO4, and evaporated under reduced pressure to obtain the title compound, which is a white solid. |