Dimethylformamide → 2-Fluoro-3-hydroxy-5-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a flask, tert-butyl(2-fluoro-5-methoxyphenoxy)dimethylsilane (6.00 g, 23 mmol), N,N,N′,N″,N″-pentamethyldiethylenetriamine (4.87 g, 28 mmol), and tetrahydrofuran (48.0 mL) were added, and the resulting mixture was cooled to −72° C. under nitrogen atmosphere. To the solution, n-butyllithium (10.2 mL, 28 mmol, 2.76 M, in hexane) was added dropwise, and the resulting mixture was stirred at −56° C. for 3 hours. To the solution, a solution of N,N-dimethylformamide (3.42 g, 47 mmol) in tetrahydrofuran (6.0 mL) was added, and the resulting mixture was warmed to 10° C., after which water was added thereto, and the two-layer reaction solution was stirred overnight at room temperature. Heptane was added to the reaction mixture, and the aqueous layer was collected. Toluene was added to the aqueous layer. To the resulting mixture, 5 N hydrochloric acid was added to adjust the pH to 2, and the resulting mixture was extracted. The organic layer was washed with water and concentrated under reduced pressure, after which a mixture of toluene and ethyl acetate was added to the resulting concentration residue, and the resulting mixture was purified by suspension. The purified product obtained was filtered and dried to obtain the captioned compound (3.16 g) as a light brown solid.

Provenance & Evidence