Uses
Reactant for:• ;Suzuki-Miyaura reactions1,2,3,4,5
Synthesis
The general procedure for the synthesis of 2,6-dimethoxyphenylboronic acid from trimethyl borate and m-phenylene dimethyl ether was as follows: 41.5 g (0.3 mol) of 1,3-dimethoxybenzene and 170 g of THF were added to a dry 1L three-neck flask. The reaction system was cooled to -30~-40°C under nitrogen protection and stirred. 240 ml (0.6 mol) of n-butyllithium in hexane solution was added slowly dropwise. After the dropwise addition, the reaction system was slowly warmed to 10~30°C and maintained at this temperature for 1 hour. Subsequently, the system was again cooled to -30~-40 °C and 62.4 g (0.6 mol) of trimethyl borate was slowly added dropwise. After the dropwise addition was completed, the reaction was maintained at this temperature for 1 hour. After the reaction was completed, 148 g of concentrated hydrochloric acid and 150 g of water were added to the system and stirred at 20-30 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure until no solvent evaporated. The residue was dissolved in 200 g of water and stirred for 20 min, followed by filtration using a Brinell funnel to give 45 g of white solid product in 90.0% yield. The product was analyzed by gas chromatography and the purity was 99.0%.
References
[1] Patent: WO2004/24738, 2004, A1. Location in patent: Page/Page column 13-14
[2] Patent: CN105348240, 2016, A. Location in patent: Paragraph 0059; 0060
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4664 - 4668
[4] Organic Letters, 2012, vol. 14, # 16, p. 4250 - 4253
[5] Patent: KR2016/90242, 2016, A. Location in patent: Paragraph 0162; 0163; 0164; 0165; 0166; 0167; 0168
