Synthesis
GENERAL STEPS: 4-Formylphenylboronic acid (4.11 g, 27.4 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL) under nitrogen protection. To this solution was added 2,2-dimethyl-1,3-propanediol (neopentyl glycol, 3.14 g, 30.1 mmol) and the reaction was stirred for 2 hours at room temperature. After completion of the reaction, the solvent was removed by rotary evaporator. The crude product obtained was dissolved in dichloromethane (120 mL) and the organic phase was washed sequentially with water (80 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 4-(5,5-dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5.66 g, 95% yield) as a white solid.
References
[1] Inorganic Chemistry, 2001, vol. 40, # 22, p. 5507 - 5517
[2] Synthesis, 1999, # 12, p. 2041 - 2044
[3] Tetrahedron, 2010, vol. 66, # 3, p. 583 - 590
[4] Patent: WO2006/67216, 2006, A2. Location in patent: Page/Page column 13
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1527 - 1532
