N-Formylmorpholine → 4-Bromo-2-(trifluoromethoxy)benzaldehyde

Temperature

-78 °C

To a stirred solution of 4-bromo-2-(trifluoromethoxy)iodobenzene (9.93 g, 28 mmol) in THF (150 mL) at -78° C. was added tert-butyllithium (37 mL of a 1.5 M solution in pentane, 56 mmol) dropwise over a period of 20 min. The pale yellow solution was stirred at -78° C. for 1.5 h when N-formylmorpholine (6.5 mL; 58 mmol) was added. The resulting solution was stirred at -78° C. for 15 min and the cooling bath was removed. The mixture was stirred for an additional 1 h, when 0.25 M aqueous citric acid (100 mL) was added. The mixture was diluted with EtOAc (150 mL), the layers were separated, the organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified using pressurized silica gel column chromatography eluting with hexane to give 4-bromo-2-(trifluoro-methoxy)benzaldehyde as a colorless liquid (TLC Rf =0.45 (hexanes)).

1. additionwas added
2. customthe cooling bath was removed
3. stirringThe mixture was stirred for an additional 1 h
4. additionwhen 0.25 M aqueous citric acid (100 mL) was added
5. additionThe mixture was diluted with EtOAc (150 mL)
6. customthe layers were separated
7. washthe organic phase was washed with brine (100 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customthe solvent was removed under reduced pressure
11. customThe residue was purified
12. washeluting with hexane

ORD record

ord-12a84a26e9b043b28ce97576a944e2bd

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090805