Diethyl Ether → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

温度

50 °C

A solution of 2-cyclopropoxy-5-(trifluoromethoxy)iodobenzene (Description 8, 0.344 g, 1 mmol) in toluene (2.5 mL) was degassed with bubbling nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium (0) (15 mg) was added, the mixture was degassed with bubbling nitrogen for a further 5 min., then carbon monoxide was bubbled through the mixture for 10 min. The mixture was warmed to 50° C. and a solution of tributyl tin hydride (0.3 mL, 1.1 mmol) in toluene (5 mL) was added at a rate of 2 mL/h. via a syringe pump, maintaining carbon monoxide bubbling throughout. The mixture was cooled, diluted with ether (20 mL) and aqueous potassium fluoride solution (50%) was added. The mixture was stirred at room temperature overnight, filtered and the layers were separated. The organic layer was dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (80:20), to give the title compound as a colourless oil. 1H NMR (360 MHz, CDCl3) δ 0.86 (4H, m), 3.82-3.9 (1H, m), 7.42 (2H, m), 7.62 (1H, d, J 2.5 Hz), and 10.36 (1H, s).

1. customthe mixture was degassed with bubbling nitrogen for a further 5 min.
2. customcarbon monoxide was bubbled through the mixture for 10 min
3. temperatureThe mixture was cooled
4. additionwas added
5. filtrationfiltered
6. customthe layers were separated
7. dry with materialThe organic layer was dried (MgSO4)
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by flash column chromatography on silica gel
10. washeluting with hexane/Et2O (80:20)

ORDレコード

ord-91770ec491f444149f0593533a433d61

出典データセット

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05919781