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

Temperature

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 record

ord-3bf8d7e6be834bbbb048583bb46c120f

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06087348