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The title compound was prepared using an adapted procedure for the same compound reported by Chaumeil et al.17 To a stirring solution of 1,3,5-trimethoxybenzene 7 (11.3 g, 67.2 mmol) in THF (200 mL) at 0 C, n-BuLi (45 mL, 1.60 M, 72.0 mmol) was added dropwise over 10 min. The resulting white suspension was stirred at this temperature for 2 h and then cooled to -78 C. B(OMe)3 (15.0 mL, 135 mmol) in THF (15 mL) was added dropwise over 1 h and the resulting mixture was stirred at -78 C for 1 h before being allowed to slowly warm in the cold bath to room temperature overnight. The resulting cloudy, white mixture was cooled to 0 C and water (100 mL) was added dropwise with stirring over 30 min. The mixture was poured into water (200 mL) and CH2Cl2 (300 mL) and stirred vigorously for 15 min. The phases were separated and the aqueous phase was extracted with CH2Cl2 (4×50 mL), and the combined organics were dried (Na2SO4), filtered and concentrated to provide a white powdery solid. The solid was dissolved in minimal boiling CHCl3 and a roughly equal portion of hot Et2O was added. The mixture was cooled to room temperature and placed in a -20 C freezer overnight to allow crystallization of the product. The resulting white crystals were isolated by suction, washed with cold Et2O (10 mL) and allowed to dry to provide 10.1 g (71%) of the desired boronic acid 9a. 1H NMR (400 MHz, CDCl3) delta 7.00 (s, 2H), 6.14 (s, 2H), 3.87 (s, 6H), 3.83 (s, 3H). NMR data for the synthesized compound corresponded to those reported for the title compound by Chaumeil et al.17
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