Dimethylformamide → 2,4-Dichloro-6-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence