反应详情

1-Bromo-2-naphthol (5.00 g, 22.4 mmol) was mixed with triisopropylsilyl chloride (7.2 mL, 33.6 mmol), DMAP (402 mg, 3.30 mmol), imidazole (3.81 g, 56.0 mmol), and pyridine (6 mL) in CH2Cl2 (50 mL). The reaction was refluxed for two hours. TLC analysis (silica, 15% EtOAc-hexanes) indicated the reaction was complete. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with CH2Cl2. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 100% hexanes) to give (1-bromo-naphthalen-2-yloxy)-triisopropyl-silane (8.4 g, 22.2 mmol) as a colorless oil in 99% yield. 1H NMR (300 MHz) CDCl3 8.21 (d, J=7.5 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.54 (m, 1H), 7.38 (m, 1H), 7.15 (d, J=8.8 Hz, 1H), 1.38 (m, 3H), 1.16 (d, J=7.1 Hz, 18H).

1. temperatureThe reaction was refluxed for two hours
2. extractionThe dilution was extracted three times with CH2Cl2
3. washwashed with brine solution
4. dry with materialdried over Na2SO4
5. filtrationfiltered through celite
6. concentrationconcentrated
7. customThe crude product was purified by flash chromatography (SiO2, 100% hexanes)