Synthesis
Using 4-bromobenzyl alcohol (compound 1, 1.0 g, 5.35 mmol) and pinacol ester of bisboronic acid (247 mg, 5.88 mmol) as raw materials, compound 1 was dissolved in 10 mL of anhydrous 1,4-dioxane under nitrogen protection, and potassium acetate and PdCl2 (Dppf) were added as catalysts. The reaction mixture was heated to 85 °C and stirred until the reaction was complete (monitored by thin layer chromatography). After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was extracted by adding ethyl acetate (200 mL) to the residue. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (mobile phase: ethyl acetate/petroleum ether = 1:8 to 1:4) to afford 181 mg of a light yellow oily liquid, 4-(hydroxymethyl)benzeneboronic acid pinacol ester, in 90% yield.
References
[1] Patent: CN108148098, 2018, A. Location in patent: Paragraph 0058; 0059; 0060
[2] Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6109 - 6121
[3] Patent: US2012/184520, 2012, A1. Location in patent: Page/Page column 17
[4] Patent: CN107445885, 2017, A. Location in patent: Paragraph 0177; 0180
[5] Patent: WO2018/98499, 2018, A1. Location in patent: Page/Page column 215
