Dimethylformamide → 2,4-Dichloro-6-methoxybenzaldehyde

Temperature

-78 °C

To a solution of 1,3-dichloro-5-methoxybenzene (1.0 g, 5.65 mmol) in THF (15 mL), cooled to −78° C., under N2 protection, was added dropwise sec-BuLi (4.18 ml of a 1.4 M solution in hexane, 5.82 mmol). After 30 minutes, anhydrous DMF (0.65 ml, 8.48 mmol) was added slowly to the solution and the mixture was stirred for at −78° C. 1.5 h. The reaction mixture was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (10:1) as eluent to give 2,4-dichloro-6-methoxybenzaldehyde as a colorless oil.

1. custom1.5 h
2. customThe reaction mixture was quenched with water
3. extractionthe aqueous layer was extracted with EtOAc
4. washThe organic layer was washed with water, brine
5. dry with materialdried with MgSO4
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. customthe residue was purified by flash chromatography

ORD record

ord-322161883c3c417288803bba04a3811a

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2