4-Nitrobenzaldehyde → 4-(2,2,2-Trifluoroethoxy)benzaldehyde

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.87 g, 21.8 mmol) in DMSO (20 ml) was added trifluoroethanol (3.97 g, 39.7 mmol) at 10-15° C. under an atmosphere of argon. The reaction mixture was stirred at this temperature for 20 min then 4-nitrobenzaldehyde (3.0 g, 19.85 mmol) was added in one portion. The reaction mixture was stirred at 10-15° C. for 3 h then at room temperature for 60 h. Brine (100 ml) was added cautiously to the reaction mixture followed by extraction with Et2O (3×70 ml). The combined organic extracts were washed with water, dried (MgSO4) and the solvent removed under reduced pressure to give an oil which was purified by flash chromatography (3:1 Hexane/EtOAc) to give a yellow oil which solidified on standing at room temperature to give the title compound (1.76 g, 43%) as a yellow solid.

1. stirringThe reaction mixture was stirred at 10-15° C. for 3 h
2. waitat room temperature for 60 h
3. extractionfollowed by extraction with Et2O (3×70 ml)
4. washThe combined organic extracts were washed with water
5. dry with materialdried (MgSO4)
6. customthe solvent removed under reduced pressure
7. customto give an oil which
8. customwas purified by flash chromatography (3:1 Hexane/EtOAc)
9. customto give a yellow oil which
10. customon standing at room temperature

ORD record

ord-8188ad2868bb4596b140c3e2cc042c02

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895313B2